Best time to book › Chicago
When is the best time to book a hotel in Chicago?
Across the 197 Chicago hotels we track, the cheapest booking window on average over the past year has been three months, at about $242 per night. That is roughly 48% less than the average same-day price of $464. Individual hotels vary, so check the hotel pages below.
Average nightly price by booking window
| Booking window | Avg. price, past year | Hotels |
|---|---|---|
| Same day | $464 | 173 |
| One week | $391 | 177 |
| One month | $329 | 175 |
| Three months | $242 | 171 |
| Six months | $440 | 164 |
Chicago hotels: when each one is cheapest
- AC Hotel Chicago Downtown
Over the last year, booking three months ahead has averaged $215 for this hotel — about $210 (49%) less than booking same day ahead, which has averaged $425. - ACME Hotel Chicago, Outset Collection by Hilton
Over the last year, booking three months ahead has averaged $130 for this hotel — about $159 (55%) less than booking same day ahead, which has averaged $289. - Aloft by Marriott Chicago Downtown River North
Over the last year, booking three months ahead has averaged $227 for this hotel — about $217 (49%) less than booking same day ahead, which has averaged $444. - Aloft by Marriott Chicago Mag Mile
Over the last year, booking three months ahead has averaged $167 for this hotel — about $216 (56%) less than booking same day ahead, which has averaged $383. - Arlo Chicago
Over the last year, booking three months ahead has averaged $198 for this hotel — about $273 (58%) less than booking same day ahead, which has averaged $471. - Best Western Grant Park Hotel
Over the last year, booking three months ahead has averaged $117 for this hotel — about $178 (60%) less than booking same day ahead, which has averaged $295. - Best Western Plus Hawthorne Terrace Hotel
Over the last year, booking one month ahead has averaged $224 for this hotel — about $264 (54%) less than booking six months ahead, which has averaged $488. - Best Western River North Hotel
Over the last year, booking three months ahead has averaged $118 for this hotel — about $150 (56%) less than booking six months ahead, which has averaged $268. - Cambria Hotel Chicago Loop - Theatre District
Over the last year, booking three months ahead has averaged $147 for this hotel — about $264 (64%) less than booking same day ahead, which has averaged $410. - Canopy by Hilton Chicago Central Loop
Over the last year, booking three months ahead has averaged $268 for this hotel — about $291 (52%) less than booking same day ahead, which has averaged $559. - Carlton Inn Midway
Over the last year, booking same day ahead has averaged $134 for this hotel — about $21 (14%) less than booking six months ahead, which has averaged $156. - Central Loop Hotel
Over the last year, booking three months ahead has averaged $154 for this hotel — about $159 (51%) less than booking six months ahead, which has averaged $313. - Chicago Athletic Association, The Unbound Collection by Hyatt
Over the last year, booking three months ahead has averaged $312 for this hotel — about $353 (53%) less than booking one week ahead, which has averaged $666. - Chicago Guest House
- Chicago Lakeshore Hotel
Over the last year, booking one month ahead has averaged $180 for this hotel — about $237 (57%) less than booking six months ahead, which has averaged $416. - Chicago Marriott Downtown Magnificent Mile
Over the last year, booking three months ahead has averaged $337 for this hotel — about $254 (43%) less than booking same day ahead, which has averaged $591. - Chicago Marriott Midway
Over the last year, booking one month ahead has averaged $230 for this hotel — about $43 (16%) less than booking same day ahead, which has averaged $272. - Chicago South Loop Hotel
Over the last year, booking one month ahead has averaged $121 for this hotel — about $44 (27%) less than booking one week ahead, which has averaged $165. - Chinatown Hotel
Over the last year, booking one week ahead has averaged $113 for this hotel — about $53 (32%) less than booking six months ahead, which has averaged $166. - CitizenM Chicago Downtown
Over the last year, booking three months ahead has averaged $168 for this hotel — about $274 (62%) less than booking same day ahead, which has averaged $443. - City Suites Hotel Chicago
Over the last year, booking three months ahead has averaged $163 for this hotel — about $86 (34%) less than booking one week ahead, which has averaged $248. - Claridge House Chicago, Tapestry Collection by Hilton
Over the last year, booking three months ahead has averaged $168 for this hotel — about $206 (55%) less than booking six months ahead, which has averaged $374. - Club Quarters Hotel Central Loop, Chicago
Over the last year, booking three months ahead has averaged $163 for this hotel — about $159 (49%) less than booking six months ahead, which has averaged $322. - Club Quarters Hotel Wacker at Michigan, Chicago
Over the last year, booking three months ahead has averaged $160 for this hotel — about $192 (55%) less than booking six months ahead, which has averaged $352. - Courtyard by Marriott Chicago at Medical District/UIC
Over the last year, booking three months ahead has averaged $185 for this hotel — about $260 (58%) less than booking same day ahead, which has averaged $445. - Courtyard by Marriott Chicago Downtown/Magnificent Mile
Over the last year, booking three months ahead has averaged $168 for this hotel — about $260 (61%) less than booking six months ahead, which has averaged $428. - Courtyard by Marriott Chicago Downtown/River North
Over the last year, booking three months ahead has averaged $190 for this hotel — about $244 (56%) less than booking six months ahead, which has averaged $434. - Crowne Plaza Chicago West Loop by IHG
Over the last year, booking three months ahead has averaged $185 for this hotel — about $267 (59%) less than booking six months ahead, which has averaged $452. - Doubletree By Hilton Chicago Midway Airport
Over the last year, booking three months ahead has averaged $207 for this hotel — about $59 (22%) less than booking six months ahead, which has averaged $265. - DoubleTree by Hilton Hotel Chicago - Magnificent Mile
Over the last year, booking three months ahead has averaged $162 for this hotel — about $212 (57%) less than booking same day ahead, which has averaged $373. - Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Over the last year, booking three months ahead has averaged $203 for this hotel — about $139 (41%) less than booking six months ahead, which has averaged $341. - Embassy Suites by Hilton Chicago Downtown River North
Over the last year, booking three months ahead has averaged $165 for this hotel — about $163 (50%) less than booking six months ahead, which has averaged $328. - Eurostars Magnificent Mile
Over the last year, booking three months ahead has averaged $131 for this hotel — about $262 (67%) less than booking same day ahead, which has averaged $392. - Fairfield by Marriott Inn & Suites Chicago Downtown/Magnificent Mile
Over the last year, booking three months ahead has averaged $165 for this hotel — about $215 (57%) less than booking six months ahead, which has averaged $380. - Fairfield by Marriott Inn & Suites Chicago Downtown/River North
Over the last year, booking three months ahead has averaged $192 for this hotel — about $731 (79%) less than booking six months ahead, which has averaged $923. - Fairmont Chicago, Millennium Park
Over the last year, booking three months ahead has averaged $263 for this hotel — about $181 (41%) less than booking six months ahead, which has averaged $443. - Four Seasons Hotel Chicago
Over the last year, booking three months ahead has averaged $622 for this hotel — about $713 (53%) less than booking same day ahead, which has averaged $1,334. - Freehand Chicago
Over the last year, booking three months ahead has averaged $108 for this hotel — about $117 (52%) less than booking same day ahead, which has averaged $225. - Hampton Inn & Suites Chicago-Downtown
Over the last year, booking three months ahead has averaged $141 for this hotel — about $239 (63%) less than booking six months ahead, which has averaged $380. - Hampton Inn by Hilton Chicago West Loop Fulton Market Area
Over the last year, booking three months ahead has averaged $252 for this hotel — about $218 (46%) less than booking same day ahead, which has averaged $469. - Hampton Inn Chicago Downtown/Magnificent Mile
Over the last year, booking three months ahead has averaged $165 for this hotel — about $206 (56%) less than booking six months ahead, which has averaged $371. - Hampton Inn Chicago Downtown/N Loop/Michigan Ave
Over the last year, booking three months ahead has averaged $115 for this hotel — about $225 (66%) less than booking same day ahead, which has averaged $341. - Hampton Inn Chicago McCormick Place
Over the last year, booking one month ahead has averaged $222 for this hotel — about $140 (39%) less than booking same day ahead, which has averaged $362. - Hampton Inn Chicago North-Loyola Station
Over the last year, booking three months ahead has averaged $167 for this hotel — about $222 (57%) less than booking same day ahead, which has averaged $389. - Hampton Inn Majestic Chicago Theatre District
Over the last year, booking three months ahead has averaged $211 for this hotel — about $205 (49%) less than booking same day ahead, which has averaged $416. - Heart O' Chicago Hotel
Over the last year, booking one month ahead has averaged $150 for this hotel — about $14 (9%) less than booking six months ahead, which has averaged $164. - HI Chicago, The J. Ira and Nicki Harris Family Hostel
Over the last year, booking one month ahead has averaged $54 for this hotel — about $20 (27%) less than booking six months ahead, which has averaged $74. - Hilton Chicago
Over the last year, booking three months ahead has averaged $235 for this hotel — about $409 (63%) less than booking same day ahead, which has averaged $645. - Hilton Chicago O'Hare Airport
Over the last year, booking three months ahead has averaged $318 for this hotel — about $193 (38%) less than booking same day ahead, which has averaged $512. - Hilton Chicago/Magnificent Mile Suites
Over the last year, booking three months ahead has averaged $179 for this hotel — about $240 (57%) less than booking one week ahead, which has averaged $419. - Hilton Garden Inn Chicago Central Loop
Over the last year, booking three months ahead has averaged $218 for this hotel — about $326 (60%) less than booking same day ahead, which has averaged $544. - Hilton Garden Inn Chicago Downtown Riverwalk
Over the last year, booking three months ahead has averaged $170 for this hotel — about $186 (52%) less than booking same day ahead, which has averaged $356. - Hilton Garden Inn Chicago Downtown South Loop
Over the last year, booking three months ahead has averaged $150 for this hotel — about $290 (66%) less than booking same day ahead, which has averaged $440. - Hilton Garden Inn Chicago Downtown/magnificent Mile
Over the last year, booking three months ahead has averaged $148 for this hotel — about $223 (60%) less than booking same day ahead, which has averaged $371. - Hilton Garden Inn Chicago McCormick Place
Over the last year, booking one month ahead has averaged $213 for this hotel — about $222 (51%) less than booking same day ahead, which has averaged $435. - Hilton Grand Vacations Club Chicago Magnificent Mile
Over the last year, booking three months ahead has averaged $204 for this hotel — about $189 (48%) less than booking six months ahead, which has averaged $392. - Hilton Vacation Club Hotel Blake Chicago
Over the last year, booking three months ahead has averaged $219 for this hotel — about $293 (57%) less than booking six months ahead, which has averaged $512. - Holiday Inn & Suites Chicago-downtown By IHG
Over the last year, booking three months ahead has averaged $166 for this hotel — about $258 (61%) less than booking six months ahead, which has averaged $425. - Holiday Inn Chicago - Midway Airport S by IHG
Over the last year, booking three months ahead has averaged $170 for this hotel — about $74 (30%) less than booking six months ahead, which has averaged $244. - Holiday Inn Chicago Dwtn - The Mart By IHG
Over the last year, booking three months ahead has averaged $262 for this hotel — about $201 (43%) less than booking six months ahead, which has averaged $463. - Holiday Inn Chicago O'hare Area By IHG
Over the last year, booking three months ahead has averaged $182 for this hotel — about $72 (28%) less than booking one month ahead, which has averaged $254. - Holiday Inn Express & Suites Chicago-Midway Airport by IHG
Over the last year, booking one month ahead has averaged $179 for this hotel — about $77 (30%) less than booking same day ahead, which has averaged $256. - Holiday Inn Express Chicago - Magnificent Mile By IHG
Over the last year, booking three months ahead has averaged $153 for this hotel — about $237 (61%) less than booking same day ahead, which has averaged $390. - Home2 Suites by Hilton Chicago McCormick Place
Over the last year, booking three months ahead has averaged $205 for this hotel — about $145 (42%) less than booking six months ahead, which has averaged $350. - Home2 Suites by Hilton Chicago River North
Over the last year, booking three months ahead has averaged $177 for this hotel — about $164 (48%) less than booking six months ahead, which has averaged $341. - Homewood Suites By Hilton Chicago Downtown South Loop
Over the last year, booking three months ahead has averaged $183 for this hotel — about $240 (57%) less than booking same day ahead, which has averaged $423. - Homewood Suites By Hilton Chicago Downtown/Magnificent Mile
Over the last year, booking three months ahead has averaged $181 for this hotel — about $184 (51%) less than booking six months ahead, which has averaged $365. - Homewood Suites By Hilton Chicago West Loop Fulton Market Area
Over the last year, booking three months ahead has averaged $220 for this hotel — about $302 (58%) less than booking same day ahead, which has averaged $522. - Homewood Suites by Hilton Chicago-Downtown
Over the last year, booking three months ahead has averaged $224 for this hotel — about $156 (41%) less than booking same day ahead, which has averaged $380. - Hotel 505 River North
Over the last year, booking three months ahead has averaged $267 for this hotel — about $313 (54%) less than booking six months ahead, which has averaged $580. - Hotel Chicago Downtown
Over the last year, booking three months ahead has averaged $286 for this hotel — about $255 (47%) less than booking six months ahead, which has averaged $541. - Hotel Chicago West Loop, Surestay Collection By Best Western
Over the last year, booking three months ahead has averaged $119 for this hotel — about $123 (51%) less than booking same day ahead, which has averaged $242. - Hotel EMC2, Autograph Collection
Over the last year, booking three months ahead has averaged $357 for this hotel — about $311 (47%) less than booking same day ahead, which has averaged $668. - Hotel Felix
Over the last year, booking three months ahead has averaged $156 for this hotel — about $134 (46%) less than booking six months ahead, which has averaged $291. - Hotel Lincoln - JDV by Hyatt
Over the last year, booking three months ahead has averaged $191 for this hotel — about $72 (27%) less than booking same day ahead, which has averaged $263. - Hotel Riu Plaza Chicago
Over the last year, booking three months ahead has averaged $210 for this hotel — about $257 (55%) less than booking six months ahead, which has averaged $468. - Hotel Saint Clair - Magnificent Mile
Over the last year, booking one month ahead has averaged $181 for this hotel — about $132 (42%) less than booking six months ahead, which has averaged $313. - Hotel Versey Chicago Lincoln Park
Over the last year, booking three months ahead has averaged $142 for this hotel — about $188 (57%) less than booking same day ahead, which has averaged $330. - Hotel Zachary, Chicago, a Tribute Portfolio Hotel
Over the last year, booking three months ahead has averaged $330 for this hotel — about $352 (52%) less than booking same day ahead, which has averaged $682. - House 5863 Bed & Breakfast
Over the last year, booking one week ahead has averaged $190 for this hotel — about $106 (36%) less than booking six months ahead, which has averaged $296. - Hyatt Centric Chicago Magnificent Mile
Over the last year, booking three months ahead has averaged $258 for this hotel — about $301 (54%) less than booking six months ahead, which has averaged $559. - Hyatt Centric The Loop Chicago
Over the last year, booking three months ahead has averaged $217 for this hotel — about $307 (59%) less than booking same day ahead, which has averaged $524. - Hyatt House Chicago / West Loop - Fulton Market
Over the last year, booking three months ahead has averaged $274 for this hotel — about $198 (42%) less than booking six months ahead, which has averaged $471. - Hyatt House Chicago Medical/University District
Over the last year, booking three months ahead has averaged $159 for this hotel — about $251 (61%) less than booking same day ahead, which has averaged $411. - Hyatt Place Chicago – Medical / University District
Over the last year, booking three months ahead has averaged $164 for this hotel — about $258 (61%) less than booking same day ahead, which has averaged $422. - Hyatt Place Chicago / River North
Over the last year, booking three months ahead has averaged $233 for this hotel — about $180 (44%) less than booking six months ahead, which has averaged $413. - Hyatt Place Chicago / Wicker Park
Over the last year, booking three months ahead has averaged $217 for this hotel — about $275 (56%) less than booking same day ahead, which has averaged $492. - Hyatt Place Chicago Downtown/the Loop
Over the last year, booking three months ahead has averaged $239 for this hotel — about $266 (53%) less than booking same day ahead, which has averaged $504. - Hyatt Place Chicago-South/University Medical Center
Over the last year, booking three months ahead has averaged $213 for this hotel — about $153 (42%) less than booking same day ahead, which has averaged $366. - Hyatt Place Chicago/Midway Airport
Over the last year, booking one month ahead has averaged $204 for this hotel — about $35 (14%) less than booking three months ahead, which has averaged $239. - Hyatt Regency Chicago
Over the last year, booking three months ahead has averaged $317 for this hotel — about $252 (44%) less than booking six months ahead, which has averaged $569. - Hyatt Regency Mccormick Place Chicago
Over the last year, booking one month ahead has averaged $364 for this hotel — about $177 (33%) less than booking six months ahead, which has averaged $541. - Inn at Lincoln Park
- Inn of Chicago Magnificent Mile
- InterContinental Chicago Magnificent Mile by IHG
Over the last year, booking three months ahead has averaged $286 for this hotel — about $278 (49%) less than booking same day ahead, which has averaged $564. - Ivy Hotel
Over the last year, booking three months ahead has averaged $126 for this hotel — about $203 (62%) less than booking same day ahead, which has averaged $329. - Jaslin Hotel
Over the last year, booking one month ahead has averaged $184 for this hotel — about $38 (17%) less than booking same day ahead, which has averaged $222. - JW Marriott Chicago
Over the last year, booking three months ahead has averaged $505 for this hotel — about $377 (43%) less than booking six months ahead, which has averaged $882. - Kasa Chicago South Loop
- Kasa Magnificent Mile Chicago
- Kimpton Gray Hotel by IHG
Over the last year, booking three months ahead has averaged $343 for this hotel — about $420 (55%) less than booking one week ahead, which has averaged $763. - Kinzie Hotel
Over the last year, booking three months ahead has averaged $141 for this hotel — about $134 (49%) less than booking one month ahead, which has averaged $274. - L7 Chicago by LOTTE
Over the last year, booking three months ahead has averaged $194 for this hotel — about $212 (52%) less than booking six months ahead, which has averaged $406. - La Quinta Inn & Suites By Wyndham Chicago Downtown
Over the last year, booking three months ahead has averaged $189 for this hotel — about $202 (52%) less than booking six months ahead, which has averaged $392. - Lang House Chicago
- Le Méridien Essex Chicago
Over the last year, booking three months ahead has averaged $185 for this hotel — about $249 (57%) less than booking six months ahead, which has averaged $434. - Level Chicago - Old Town
Over the last year, booking three months ahead has averaged $281 for this hotel — about $204 (42%) less than booking one week ahead, which has averaged $485. - Level Chicago - River North
Over the last year, booking three months ahead has averaged $273 for this hotel — about $269 (50%) less than booking six months ahead, which has averaged $542. - Loews Chicago Hotel
Over the last year, booking three months ahead has averaged $286 for this hotel — about $414 (59%) less than booking six months ahead, which has averaged $700. - LondonHouse Chicago, Curio Collection by Hilton
Over the last year, booking three months ahead has averaged $261 for this hotel — about $359 (58%) less than booking same day ahead, which has averaged $620. - Longman & Eagle
- Magnolia Studios
- Majestic Hotel Chicago
Over the last year, booking three months ahead has averaged $172 for this hotel — about $126 (42%) less than booking same day ahead, which has averaged $298. - Manilow Suites At North Harbor Tower
- Marriott Chicago O’hare
Over the last year, booking three months ahead has averaged $263 for this hotel — about $178 (40%) less than booking same day ahead, which has averaged $441. - Marriott Marquis Chicago
Over the last year, booking three months ahead has averaged $415 for this hotel — about $251 (38%) less than booking same day ahead, which has averaged $666. - Moxy Chicago Downtown
Over the last year, booking three months ahead has averaged $215 for this hotel — about $191 (47%) less than booking same day ahead, which has averaged $406. - Nobu Hotel Chicago
Over the last year, booking three months ahead has averaged $499 for this hotel — about $672 (57%) less than booking same day ahead, which has averaged $1,170. - Ohio House Motel
Over the last year, booking three months ahead has averaged $111 for this hotel — about $113 (50%) less than booking six months ahead, which has averaged $224. - Omni Chicago Hotel
Over the last year, booking three months ahead has averaged $269 for this hotel — about $239 (47%) less than booking same day ahead, which has averaged $508. - Palmer House a Hilton Hotel
Over the last year, booking three months ahead has averaged $254 for this hotel — about $278 (52%) less than booking same day ahead, which has averaged $532. - Park Hyatt Chicago
Over the last year, booking three months ahead has averaged $623 for this hotel — about $809 (56%) less than booking same day ahead, which has averaged $1,432. - Pendry Chicago
Over the last year, booking three months ahead has averaged $328 for this hotel — about $460 (58%) less than booking six months ahead, which has averaged $787. - Radisson Blu Aqua Chicago
Over the last year, booking three months ahead has averaged $257 for this hotel — about $199 (44%) less than booking six months ahead, which has averaged $456. - Ray's Bucktown Bed and Breakfast
Over the last year, booking three months ahead has averaged $281 for this hotel — about $127 (31%) less than booking one month ahead, which has averaged $408. - Renaissance Chicago Downtown Hotel
Over the last year, booking three months ahead has averaged $366 for this hotel — about $341 (48%) less than booking same day ahead, which has averaged $707. - Renaissance Chicago O'Hare Suites Hotel
Over the last year, booking one month ahead has averaged $235 for this hotel — about $118 (34%) less than booking same day ahead, which has averaged $353. - Residence Inn by Marriott Chicago Downtown Magnificent Mile
Over the last year, booking three months ahead has averaged $224 for this hotel — about $269 (55%) less than booking six months ahead, which has averaged $493. - Residence Inn by Marriott Chicago Downtown/Loop
Over the last year, booking three months ahead has averaged $258 for this hotel — about $366 (59%) less than booking same day ahead, which has averaged $624. - Residence Inn by Marriott Chicago Downtown/River North
Over the last year, booking three months ahead has averaged $235 for this hotel — about $285 (55%) less than booking same day ahead, which has averaged $520. - River Hotel Chicago
Over the last year, booking three months ahead has averaged $159 for this hotel — about $185 (54%) less than booking same day ahead, which has averaged $344. - Rodeway Inn
Over the last year, booking one month ahead has averaged $104 for this hotel — about $12 (10%) less than booking same day ahead, which has averaged $116. - Roscoe Village Guesthouse
- Ruby Room
- Sable at Navy Pier Chicago, Curio Collection by Hilton
Over the last year, booking three months ahead has averaged $240 for this hotel — about $292 (55%) less than booking same day ahead, which has averaged $531. - Sentral Michigan Avenue
Over the last year, booking three months ahead has averaged $179 for this hotel — about $173 (49%) less than booking same day ahead, which has averaged $351. - Sheraton Grand Chicago Riverwalk
Over the last year, booking three months ahead has averaged $299 for this hotel — about $324 (52%) less than booking six months ahead, which has averaged $623. - Silversmith Hotel Chicago Downtown
Over the last year, booking three months ahead has averaged $235 for this hotel — about $134 (36%) less than booking six months ahead, which has averaged $369. - Sofitel Chicago Magnificent Mile
Over the last year, booking three months ahead has averaged $330 for this hotel — about $322 (49%) less than booking one week ahead, which has averaged $652. - Soho House Chicago
- Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Over the last year, booking six months ahead has averaged $248 for this hotel — about $129 (34%) less than booking same day ahead, which has averaged $377. - Sophy-Hyde Park
Over the last year, booking three months ahead has averaged $321 for this hotel — about $243 (43%) less than booking one week ahead, which has averaged $564. - Sports Illustrated Resorts Chicago
Over the last year, booking three months ahead has averaged $209 for this hotel — about $201 (49%) less than booking same day ahead, which has averaged $409. - SpringHill Suites by Marriott
Over the last year, booking three months ahead has averaged $231 for this hotel — about $243 (51%) less than booking six months ahead, which has averaged $473. - SpringHill Suites by Marriott Chicago Chinatown
Over the last year, booking three months ahead has averaged $200 for this hotel — about $185 (48%) less than booking same day ahead, which has averaged $385. - SpringHill Suites by Marriott Chicago O'Hare
Over the last year, booking three months ahead has averaged $194 for this hotel — about $128 (40%) less than booking same day ahead, which has averaged $322. - Staypineapple, An Iconic Hotel, The Loop Chicago
Over the last year, booking three months ahead has averaged $259 for this hotel — about $234 (47%) less than booking same day ahead, which has averaged $493. - Super 8 by Wyndham Chicago IL
Over the last year, booking three months ahead has averaged $172 for this hotel — about $53 (24%) less than booking six months ahead, which has averaged $226. - Swissôtel Chicago
Over the last year, booking one month ahead has averaged $324 for this hotel — about $294 (48%) less than booking six months ahead, which has averaged $618. - The Allegro Royal Sonesta Hotel Chicago Loop
Over the last year, booking three months ahead has averaged $214 for this hotel — about $284 (57%) less than booking same day ahead, which has averaged $498. - The Amber Inn
- The Blackstone, Autograph Collection
Over the last year, booking three months ahead has averaged $368 for this hotel — about $223 (38%) less than booking same day ahead, which has averaged $591. - The Buckingham Hotel
Over the last year, booking three months ahead has averaged $224 for this hotel — about $152 (40%) less than booking same day ahead, which has averaged $376. - The Chicago Hotel Collection Millennium Park
- The Chicago Hotel Collection River North
Over the last year, booking three months ahead has averaged $121 for this hotel — about $335 (73%) less than booking six months ahead, which has averaged $455. - The Chicago Hotel Collection Wrigleyville
Over the last year, booking three months ahead has averaged $119 for this hotel — about $3,066 (96%) less than booking same day ahead, which has averaged $3,185. - The Congress Plaza Hotel & Convention Center
Over the last year, booking three months ahead has averaged $157 for this hotel — about $123 (44%) less than booking six months ahead, which has averaged $280. - The Drake
Over the last year, booking three months ahead has averaged $194 for this hotel — about $197 (50%) less than booking six months ahead, which has averaged $391. - The Emily Hotel
Over the last year, booking three months ahead has averaged $253 for this hotel — about $400 (61%) less than booking one week ahead, which has averaged $653. - The Flats at Loyola Station
- The Godfrey Hotel Chicago
Over the last year, booking three months ahead has averaged $175 for this hotel — about $158 (47%) less than booking six months ahead, which has averaged $333. - The Guesthouse Hotel
- The Gwen, a Luxury Collection Hotel
Over the last year, booking three months ahead has averaged $488 for this hotel — about $379 (44%) less than booking one week ahead, which has averaged $867. - The Hotel at Midtown
Over the last year, booking one month ahead has averaged $349 for this hotel — about $260 (43%) less than booking same day ahead, which has averaged $609. - The Hoxton Chicago
Over the last year, booking three months ahead has averaged $299 for this hotel — about $455 (60%) less than booking one week ahead, which has averaged $754. - The Langham, Chicago
Over the last year, booking three months ahead has averaged $658 for this hotel — about $709 (52%) less than booking one week ahead, which has averaged $1,367. - The LaSalle Chicago, Autograph Collection
Over the last year, booking three months ahead has averaged $388 for this hotel — about $469 (55%) less than booking same day ahead, which has averaged $857. - THE MIDLAND HOTEL, Chicago, A Tribute Portfolio Hotel
Over the last year, booking one month ahead has averaged $250 for this hotel — about $295 (54%) less than booking six months ahead, which has averaged $545. - The Neighborhood Hotel Lincoln Park
Over the last year, booking same day ahead has averaged $282 for this hotel — about $61 (18%) less than booking one month ahead, which has averaged $343. - The Neighborhood Hotel Little Italy
- The Peninsula Chicago
Over the last year, booking three months ahead has averaged $625 for this hotel — about $951 (60%) less than booking one week ahead, which has averaged $1,576. - The Publishing House Bed and Breakfast
- The Ritz-Carlton, Chicago
Over the last year, booking three months ahead has averaged $594 for this hotel — about $639 (52%) less than booking same day ahead, which has averaged $1,234. - The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel
Over the last year, booking three months ahead has averaged $223 for this hotel — about $232 (51%) less than booking same day ahead, which has averaged $455. - The Robey
Over the last year, booking three months ahead has averaged $329 for this hotel — about $265 (45%) less than booking same day ahead, which has averaged $594. - The Royal Sonesta Chicago Downtown
Over the last year, booking three months ahead has averaged $232 for this hotel — about $368 (61%) less than booking same day ahead, which has averaged $600. - The Sono Chicago
Over the last year, booking same day ahead has averaged $221 for this hotel — about $58 (21%) less than booking one week ahead, which has averaged $279. - The St. Regis Chicago
Over the last year, booking one month ahead has averaged $961 for this hotel — about $873 (48%) less than booking same day ahead, which has averaged $1,834. - The Study at University of Chicago
Over the last year, booking one month ahead has averaged $335 for this hotel — about $98 (23%) less than booking one week ahead, which has averaged $432. - The Villa Toscana
Over the last year, booking same day ahead has averaged $103 for this hotel — about $188 (65%) less than booking six months ahead, which has averaged $291. - The Wade
Over the last year, booking three months ahead has averaged $196 for this hotel — about $282 (59%) less than booking six months ahead, which has averaged $478. - The Westin Chicago River North
Over the last year, booking three months ahead has averaged $338 for this hotel — about $619 (65%) less than booking one week ahead, which has averaged $957. - The Westin Michigan Avenue Chicago
Over the last year, booking three months ahead has averaged $234 for this hotel — about $232 (50%) less than booking same day ahead, which has averaged $466. - The Wheeler Mansion
- The Whitehall Hotel, BW Premier Collection
Over the last year, booking three months ahead has averaged $127 for this hotel — about $144 (53%) less than booking same day ahead, which has averaged $271. - theWit Chicago, a Hilton Hotel
Over the last year, booking three months ahead has averaged $231 for this hotel — about $410 (64%) less than booking same day ahead, which has averaged $641. - Travelodge by Wyndham Downtown Chicago
Over the last year, booking one month ahead has averaged $135 for this hotel — about $79 (37%) less than booking six months ahead, which has averaged $213. - Trump International Hotel & Tower Chicago
Over the last year, booking three months ahead has averaged $382 for this hotel — about $632 (62%) less than booking same day ahead, which has averaged $1,014. - Union League Club of Chicago
- University Club of Chicago
- Villa D' Citta
Over the last year, booking three months ahead has averaged $311 for this hotel — about $102 (25%) less than booking six months ahead, which has averaged $413. - voco Chicago Downtown - Riverwalk by IHG
Over the last year, booking three months ahead has averaged $283 for this hotel — about $166 (37%) less than booking one week ahead, which has averaged $449. - Waldorf Astoria Chicago
Over the last year, booking three months ahead has averaged $623 for this hotel — about $769 (55%) less than booking one week ahead, which has averaged $1,393. - Warwick Allerton - Chicago
Over the last year, booking three months ahead has averaged $136 for this hotel — about $305 (69%) less than booking one week ahead, which has averaged $440. - Wicker Park Inn
Over the last year, booking three months ahead has averaged $360 for this hotel — about $38 (10%) less than booking same day ahead, which has averaged $398. - Willows Hotel Chicago
Over the last year, booking three months ahead has averaged $140 for this hotel — about $178 (56%) less than booking same day ahead, which has averaged $317. - Wrigley Hostel
Over the last year, booking one month ahead has averaged $38 for this hotel — about $19 (34%) less than booking same day ahead, which has averaged $57.
Common questions
When is the best time to book a hotel in Chicago?
Across the 197 Chicago hotels we track, the cheapest booking window on average over the past year has been three months, at about $242 per night. That is roughly 48% less than the average same-day price of $464. Individual hotels vary, so check the hotel pages below.
Is it cheaper to book a hotel in Chicago early or last minute?
Compare the booking windows in the table: it shows the average nightly price across tracked Chicago hotels when booked same day, one week, one month, three months and six months ahead.
How does RateWatchers know?
We record each hotel's price every day, as it would appear to someone booking that day and for each of several lead times ahead of the stay. Prices come from booking providers and are a guide, not a guarantee.