Cheapest time to visit Chicago
As of Oct 2026, TravelDeals’ own measurements show Chicago hotels are cheapest in January — $193 median a night, against $580 in June.
November median: $266 per night across 143 tracked hotels. Measured one-night stays for two adults.
December median: $199 per night across 143 tracked hotels. Measured one-night stays for two adults.
January median: $193 per night across 142 tracked hotels. Measured one-night stays for two adults.
February median: $195 per night across 139 tracked hotels. Measured one-night stays for two adults.
March median: $252 per night across 138 tracked hotels. Measured one-night stays for two adults.
April median: $359 per night across 132 tracked hotels. Measured one-night stays for two adults.
May median: $413 per night across 131 tracked hotels. Measured one-night stays for two adults.
June median: $580 per night across 126 tracked hotels. Measured one-night stays for two adults.
July median: $496 per night across 124 tracked hotels. Measured one-night stays for two adults.
August median: $470 per night across 117 tracked hotels. Measured one-night stays for two adults.
September median: $514 per night across 108 tracked hotels. Measured one-night stays for two adults.
Next 11 months · 10,152 prices · all prices in USD
The year ahead
median USD per night · one-night stays for two adultsLowerNear averageHigherYear average $358/night
Select a bar to change month. The current month covers remaining dates.
Hotels below their usual price in November
Hotels below their usual price in December
Hotels below their usual price in January
Hotels below their usual price in February
Hotels below their usual price in March
Hotels below their usual price in April
Hotels below their usual price in May
Hotels below their usual price in June
Hotels below their usual price in July
Hotels below their usual price in August
Hotels below their usual price in September
Sorted by biggest drop from each hotel’s 12-month median.November 2026143 hotels · median $266/night
$136 or less$904 or more
About these prices
Recorded nightly prices across 143 Chicago hotels in November. Taller bars mean more price checks in that range, not more unique hotels. The highlighted range contains the median of $266 per night.
November: 143 hotels, median $266 a night, from 927 prices.
December 2026143 hotels · median $199/night
$136 or less$904 or more
About these prices
Recorded nightly prices across 143 Chicago hotels in December. Taller bars mean more price checks in that range, not more unique hotels. The highlighted range contains the median of $199 per night.
December: 143 hotels, median $199 a night, from 1095 prices.
January 2027142 hotels · median $193/night
$136 or less$904 or more
About these prices
Recorded nightly prices across 142 Chicago hotels in January. Taller bars mean more price checks in that range, not more unique hotels. The highlighted range contains the median of $193 per night.
January: 142 hotels, median $193 a night, from 1082 prices.
February 2027139 hotels · median $195/night
$136 or less$904 or more
About these prices
Recorded nightly prices across 139 Chicago hotels in February. Taller bars mean more price checks in that range, not more unique hotels. The highlighted range contains the median of $195 per night.
February: 139 hotels, median $195 a night, from 939 prices.
March 2027138 hotels · median $252/night
$136 or less$904 or more
About these prices
Recorded nightly prices across 138 Chicago hotels in March. Taller bars mean more price checks in that range, not more unique hotels. The highlighted range contains the median of $252 per night.
March: 138 hotels, median $252 a night, from 1042 prices.
April 2027132 hotels · median $359/night
$136 or less$904 or more
About these prices
Recorded nightly prices across 132 Chicago hotels in April. Taller bars mean more price checks in that range, not more unique hotels. The highlighted range contains the median of $359 per night.
April: 132 hotels, median $359 a night, from 868 prices.
May 2027131 hotels · median $413/night
$136 or less$904 or more
About these prices
Recorded nightly prices across 131 Chicago hotels in May. Taller bars mean more price checks in that range, not more unique hotels. The highlighted range contains the median of $413 per night.
May: 131 hotels, median $413 a night, from 959 prices.
June 2027126 hotels · median $580/night
$136 or less$904 or more
About these prices
Recorded nightly prices across 126 Chicago hotels in June. Taller bars mean more price checks in that range, not more unique hotels. The highlighted range contains the median of $580 per night.
June: 126 hotels, median $580 a night, from 767 prices.
July 2027124 hotels · median $496/night
$136 or less$904 or more
About these prices
Recorded nightly prices across 124 Chicago hotels in July. Taller bars mean more price checks in that range, not more unique hotels. The highlighted range contains the median of $496 per night.
July: 124 hotels, median $496 a night, from 886 prices.
August 2027117 hotels · median $470/night
$136 or less$904 or more
About these prices
Recorded nightly prices across 117 Chicago hotels in August. Taller bars mean more price checks in that range, not more unique hotels. The highlighted range contains the median of $470 per night.
August: 117 hotels, median $470 a night, from 897 prices.
September 2027108 hotels · median $514/night
$136 or less$904 or more
About these prices
Recorded nightly prices across 108 Chicago hotels in September. Taller bars mean more price checks in that range, not more unique hotels. The highlighted range contains the median of $514 per night.
September: 108 hotels, median $514 a night, from 690 prices.
12 hotels are below their own usual price in November, furthest below first.
The Wade
JW Marriott Chicago
Hyatt Place Chicago/Downtown - The Loop
voco Chicago Downtown - Riverwalk by IHG
Crowne Plaza - Chicago West Loop by IHG
Hotel 55 Chicago Downtown
Hilton Vacation Club Hotel Blake Chicago
Millennium Hotel Knickerbocker Chicago
Best Western Grant Park Hotel
Aloft by Marriott Chicago Downtown River North
Freehand Chicago
Springhill Suites by Marriott Chicago Downtown/ River North
No hotels in this Chicago shortlist are in the under $100 range in November. Closest to your budget: $100–200.
No hotels in this Chicago shortlist are in the $400+ range in November. Closest to your budget: $200–400.
12 hotels are below their own usual price in December, furthest below first.
Hyatt Place Chicago Medical/University District
Courtyard by Marriott Chicago at Medical District-UIC- Hotel 55 Chicago Downtown
- voco Chicago Downtown - Riverwalk by IHG
- Crowne Plaza - Chicago West Loop by IHG
- Best Western Grant Park Hotel
citizenM Chicago Downtown
Club Quarters Hotel Wacker at Michigan, Chicago
Canopy By Hilton Chicago Central Loop
River Hotel
Holiday Inn Express Chicago - Magnificent Mile by IHG- Aloft by Marriott Chicago Downtown River North
No hotels in this Chicago shortlist are in the $400+ range in December. Closest to your budget: $200–400.
12 hotels are below their own usual price in January, furthest below first.
- Hyatt Place Chicago Medical/University District
- citizenM Chicago Downtown
- Crowne Plaza - Chicago West Loop by IHG
Hampton Inn Chicago Downtown/N Loop/Michigan Ave- voco Chicago Downtown - Riverwalk by IHG
- Best Western Grant Park Hotel
Courtyard by Marriott Chicago Downtown/River North- Courtyard by Marriott Chicago at Medical District-UIC
Level Chicago - Fulton Market
Chicago Lake Shore Hotel- Aloft by Marriott Chicago Downtown River North
- River Hotel
No hotels in this Chicago shortlist are in the $400+ range in January. Closest to your budget: $200–400.
12 hotels are below their own usual price in February, furthest below first.
- Hyatt Place Chicago/Downtown - The Loop
- River Hotel
- citizenM Chicago Downtown
- Hampton Inn Chicago Downtown/N Loop/Michigan Ave
- voco Chicago Downtown - Riverwalk by IHG
- Chicago Lake Shore Hotel
- Crowne Plaza - Chicago West Loop by IHG
Le Meridien Essex Chicago
Sports Illustrated Resorts Chicago- Best Western Grant Park Hotel
Arlo Chicago
Cambria Hotel Chicago Loop - Theatre District
No hotels in this Chicago shortlist are in the under $100 range in February. Closest to your budget: $100–200.
No hotels in this Chicago shortlist are in the $400+ range in February. Closest to your budget: $200–400.
12 hotels are below their own usual price in March, furthest below first.
- Chicago Lake Shore Hotel
Central Loop Hotel
Warwick Allerton Chicago- River Hotel
- Club Quarters Hotel Wacker at Michigan, Chicago
- Crowne Plaza - Chicago West Loop by IHG
- voco Chicago Downtown - Riverwalk by IHG
- Hyatt Place Chicago/Downtown - The Loop
- Le Meridien Essex Chicago
The Palmer House Hilton
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
The Peninsula Chicago
No hotels in this Chicago shortlist are in the under $100 range in March. Closest to your budget: $100–200.
12 hotels are below their own usual price in April, furthest below first.
- The Peninsula Chicago
Four Seasons Chicago
Eurostars Magnificent Mile
Pendry Chicago
Nobu Hotel Chicago
The Hoxton, Chicago
Park Hyatt Chicago
Omni Chicago Hotel
Hotel EMC2, Autograph Collection
Hampton Inn Chicago-Midway Airport
Hyatt Regency McCormick Place Chicago
Hotel Versey Chicago Lincoln Park
No hotels in this Chicago shortlist are in the under $100 range in April. Closest to your budget: $100–200.
1 hotels are below their own usual price in May, furthest below first.
No hotels in this Chicago shortlist are in the under $100 range in May. Closest to your budget: $200–400.
No hotels in this Chicago shortlist are in the $100–200 range in May. Closest to your budget: $200–400.
No hotels in this Chicago shortlist are in the $400+ range in May. Closest to your budget: $200–400.
No hotel we track in Chicago is below its own usual price in June.
No hotel we track in Chicago is below its own usual price in July.
1 hotels are below their own usual price in August, furthest below first.
No hotels in this Chicago shortlist are in the under $100 range in August. Closest to your budget: $200–400.
No hotels in this Chicago shortlist are in the $100–200 range in August. Closest to your budget: $200–400.
No hotels in this Chicago shortlist are in the $400+ range in August. Closest to your budget: $200–400.
No hotel we track in Chicago is below its own usual price in September.
Which nights
median by arrival day, across every hotel we track and all twelve monthsArriving on a Monday instead of a Tuesday saves 23% at the Chicago median — $88 a night, on the same hotels. Measured across 10,152 forward prices.
Every hotel we track in Chicago
143 tracked hotels · compare locations and measured pricesChecked rate: one refundable night, 30 days aheadMap all hotels ↑- Freehand Chicago · 45 nights measured4★$105
- Hilton Garden Inn Chicago McCormick Place · 29 nights measured3★$123
- Warwick Allerton Chicago · 42 nights measured4★$125
- Hyatt House Chicago Medical/University District · 45 nights measured4★$127
- The Chicago Hotel Collection River North · 43 nights measured3★$134
- Home2 Suites By Hilton Chicago McCormick Place · 21 nights measured3★$144
- Holiday Inn & Suites Chicago-Downtown by IHG · 42 nights measured3★$153
- Hilton Garden Inn Chicago/Midway Airport · 45 nights measured3★$157
- Kinzie Hotel · 40 nights measured4★$165
- Best Western Grant Park Hotel · 35 nights measured3★$167
- Hampton Inn Chicago-Midway Airport · 45 nights measured3★$168
- Crowne Plaza - Chicago West Loop by IHG · 45 nights measured3★$169
- Fairfield Inn and Suites Chicago Downtown-River North · 44 nights measured3★$170
- The Palmer House Hilton · 39 nights measured4★$174
- Millennium Hotel Knickerbocker Chicago · 43 nights measured4★$181
- Hotel Felix · 45 nights measured4★$182
- Le Meridien Essex Chicago · 41 nights measured4★$183
- Swissotel Chicago · 37 nights measured4★$185
- SpringHill Suites by Marriott Chicago Chinatown · 38 nights measured3★$187
- Congress Plaza Hotel · 45 nights measured3★$189
- Staypineapple, An Iconic Hotel, The Loop · 45 nights measured4★$192
- ACME Hotel Chicago, Outset Collection by Hilton · 42 nights measured4★$198
- Hyatt House Chicago West Loop-Fulton Market · 40 nights measured3★$199
- Hotel Saint Clair - Magnificent Mile · 41 nights measured4★$199
- The Whitehall Hotel - BW Premier Collection · 42 nights measured3★$200
- Courtyard by Marriott Chicago at Medical District-UIC · 38 nights measured3★$200
- Cambria Hotel Chicago Loop - Theatre District · 40 nights measured4★$201
- Best Western Chicago Downtown-River North · 44 nights measured3★$204
- Jaslin Hotel · 33 nights measured3★$205
- Hyatt Place Chicago Medical/University District · 45 nights measured4★$206
Show the other 113 hotels
- Hampton Inn & Suites Chicago Medical District Uic · 45 nights measured3★$207
- Homewood Suites by Hilton Chicago Downtown - Magnificent Mile · 40 nights measured3★$208
- Hilton Chicago/Oak Lawn · 45 nights measured3★$210
- Holiday Inn Express Chicago - Magnificent Mile by IHG · 44 nights measured3★$211
- Home2 Suites By Hilton Chicago River North · 45 nights measured3★$216
- Hilton Garden Inn Chicago Downtown/Magnificent Mile · 41 nights measured3★$217
- Hilton Garden Inn- Chicago Central Loop · 39 nights measured3★$218
- voco Chicago Downtown - Riverwalk by IHG · 44 nights measured3★$218
- Courtyard Chicago Downtown/Magnificent Mile · 44 nights measured4★$219
- Moxy Chicago Downtown · 45 nights measured3★$220
- The Allegro Royal Sonesta Hotel Chicago Loop · 42 nights measured4★$225
- Arlo Chicago · 45 nights measured4★$226
- Silversmith Hotel Chicago Downtown · 39 nights measured4★$228
- Courtyard by Marriott Chicago Downtown/River North · 41 nights measured3★$228
- Hampton Inn Chicago Downtown/Magnificent Mile · 41 nights measured3★$229
- Hyatt Centric The Loop Chicago · 43 nights measured4★$230
- Hampton Inn Chicago McCormick Place · 28 nights measured3★$231
- La Quinta Inn & Suites by Wyndham Chicago Downtown · 43 nights measured3★$233
- Residence Inn Chicago Downtown/Loop · 45 nights measured3★$234
- Hampton Inn Chicago Downtown/N Loop/Michigan Ave · 28 nights measured3★$236
- Chicago Lake Shore Hotel · 45 nights measured3★$236
- Aloft Chicago Mag Mile · 43 nights measured3★$237
- Fairfield Inn and Suites Chicago Downtown/ Magnificent Mile · 43 nights measured3★$240
- Sports Illustrated Resorts Chicago · 42 nights measured4★$241
- The Royal Sonesta Chicago River North · 35 nights measured4★$242
- Hilton Garden Inn Chicago Downtown South Loop · 39 nights measured3★$242
- Hyatt Regency McCormick Place Chicago · 38 nights measured4★$242
- Ivy Boutique Hotel · 45 nights measured4★$243
- Chicago South Loop Hotel · 45 nights measured3★$244
- The Buckingham Hotel · 34 nights measured3★$248
- Eurostars Magnificent Mile · 45 nights measured4★$253
- Homewood Suites by Hilton Chicago-Downtown · 38 nights measured3★$254
- Hilton Grand Vacations Club Chicago Magnificent Mile · 33 nights measured3★$254
- Sophy Hyde Park · 39 nights measured4★$256
- Homewood Suites By Hilton Chicago Downtown South Loop · 38 nights measured3★$259
- River Hotel · 38 nights measured4★$260
- Central Loop Hotel · 33 nights measured4★$260
- Hotel Versey Chicago Lincoln Park · 37 nights measured3★$261
- Hampton Inn Majestic Chicago Theatre District · 33 nights measured3★$262
- Sonesta ES Suites Chicago Downtown Magnificent Mile Medical · 40 nights measured3★$263
- Club Quarters Hotel Wacker at Michigan, Chicago · 37 nights measured4★$265
- Hyatt Place Chicago/Downtown - The Loop · 44 nights measured3★$270
- DoubleTree by Hilton Chicago Magnificent Mile · 41 nights measured4★$272
- Radisson Blu Aqua Hotel, Chicago · 43 nights measured4★$274
- Hilton Garden Inn Chicago Downtown Riverwalk · 43 nights measured3★$275
- The Godfrey Hotel Chicago · 45 nights measured4★$280
- Sheraton Grand Chicago Riverwalk · 40 nights measured4★$281
- The Royal Sonesta Chicago Downtown · 42 nights measured4★$282
- JW Marriott Chicago · 41 nights measured5★$283
- Chicago Marriott Downtown Magnificent Mile · 39 nights measured4★$286
- Hyatt Place Chicago-South/University Medical Center · 40 nights measured3★$288
- Aloft by Marriott Chicago Downtown River North · 43 nights measured3★$289
- Canopy By Hilton Chicago Central Loop · 37 nights measured4★$289
- Hampton Inn Chicago West Loop Fulton Market Area · 43 nights measured3★$289
- citizenM Chicago Downtown · 45 nights measured4★$293
- AC Hotel Chicago Downtown · 43 nights measured4★$293
- Embassy Suites by Hilton Chicago Downtown Magnificent Mile · 40 nights measured4★$294
- Hilton Chicago Magnificent Mile Suites · 45 nights measured3★$294
- Springhill Suites by Marriott Chicago Downtown/ River North · 45 nights measured3★$295
- City Suites Hotel · 45 nights measured3★$297
- Sentral Michigan Avenue · 45 nights measured3★$298
- Hampton Inn & Suites Chicago-Downtown · 36 nights measured3★$299
- Sable At Navy Pier Chicago, Curio Collection By Hilton · 45 nights measured4★$300
- Hotel Chicago Downtown, Autograph Collection · 43 nights measured4★$301
- Embassy Suites Chicago - Downtown River North · 41 nights measured3★$304
- theWit Chicago, a Hilton Hotel · 32 nights measured4★$305
- Hyatt Regency Chicago · 39 nights measured4★$306
- Residence Inn by Marriott Chicago Downtown / River North · 45 nights measured3★$307
- Claridge House Chicago, Tapestry Collection by Hilton · 43 nights measured4★$307
- L7 Chicago by LOTTE · 41 nights measured4★$313
- Hyatt Place Chicago River North · 44 nights measured3★$315
- Hampton Inn Chicago North-Loyola Station · 44 nights measured3★$323
- Hyatt Centric Chicago Magnificent Mile · 36 nights measured4★$324
- InterContinental Chicago Magnificent Mile by IHG · 42 nights measured4★$325
- The Westin Michigan Avenue Chicago · 42 nights measured4★$328
- Marriott Marquis Chicago · 41 nights measured4★$331
- The Hoxton, Chicago · 37 nights measured4★$337
- The Emily Hotel · 37 nights measured4★$337
- Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area · 45 nights measured3★$337
- Hotel 55 Chicago Downtown · 45 nights measured4★$345
- Level Chicago - Fulton Market · 45 nights measured5★$347
- Hotel Lincoln · 36 nights measured4★$348
- The Drake Hotel · 29 nights measured4★$349
- Omni Chicago Hotel · 38 nights measured4★$350
- LondonHouse Chicago, Curio Collection by Hilton · 44 nights measured4★$350
- Hilton Vacation Club Hotel Blake Chicago · 23 nights measured5★$366
- THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel · 44 nights measured4★$375
- The Majestic Hotel · 45 nights measured3★$376
- The Willows Hotel · 45 nights measured3★$376
- Riu Plaza Chicago · 39 nights measured4★$385
- Residence Inn by Marriott Chicago Downtown Magnificent Mile · 42 nights measured3★$399
- Renaissance Chicago Downtown Hotel · 43 nights measured4★$409
- Pendry Chicago · 44 nights measured4★$412
- Loews Chicago Hotel · 41 nights measured4★$414
- Best Western Plus Hawthorne Terrace Hotel · 32 nights measured3★$459
- Sofitel Chicago Magnificent Mile · 42 nights measured5★$486
- Hyatt Place Chicago Wicker Park · 34 nights measured3★$491
- Viceroy Chicago · 43 nights measured5★$519
- Nobu Hotel Chicago · 42 nights measured5★$526
- The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago · 44 nights measured4★$528
- Hotel Zachary, Chicago, a Tribute Portfolio Hotel · 41 nights measured4★$528
- Hotel EMC2, Autograph Collection · 44 nights measured4★$541
- The Ritz-Carlton, Chicago · 42 nights measured5★$586
- Trump International Hotel & Tower Chicago · 45 nights measured5★$594
- The Robey, Chicago, a Member of Design Hotels · 37 nights measured4★$653
- Park Hyatt Chicago · 44 nights measured5★$658
- The St. Regis Chicago · 45 nights measured5★$816
- Thompson Chicago, by Hyatt · 44 nights measured4★$890
- The Langham Chicago · 39 nights measured5★$896
- Waldorf Astoria Chicago · 44 nights measured5★$932
- The Peninsula Chicago · 45 nights measured5★$985
- The Wade · 45 nights measured4★$1,601
- Four Seasons Chicago · 44 nights measured5★$1,636
Recent Chicago deal records
- THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel$85 total1 night from 22 Nov 202678% below · 40 nights
- Residence Inn by Marriott Chicago Downtown / River North$1,820 total7 nights from 27 Nov 202637% below · 45 nights
Watch Chicago
We email you when a month here gets materially cheaper. Nothing else — no digest, no weekly send.
Continue with your account, then review where and when to watch. Weekly deal emails are optional.
How we work this out
Every hotel here is priced once a week for the same stay — one refundable night, two adults — on dates spread across the next twelve months. Holding the room and the party the same is what makes a change in the answer mean something; how far ahead each date sits is the one thing we vary on purpose, because that is the question this page answers — which month to go, not how early to book. Every figure is a one-night stay as quoted, never a longer total divided down. The longer version.