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Cities · Chicago

Cheapest time to visit Chicago

We price 143 Chicago hotels every night, and once a week we price dates across the coming year. The twelve-month picture appears after the next weekly sweep.

Every hotel we track in Chicago

143 tracked hotels · compare locations and measured prices
  1. The Chicago Hotel Collection River North · 19 nights measured3★$61
  2. Millennium Hotel Knickerbocker Chicago · 21 nights measured4★$130
  3. Freehand Chicago · 21 nights measured4★$134
  4. Warwick Allerton Chicago · 18 nights measured4★$137
  5. The Whitehall Hotel - BW Premier Collection · 18 nights measured3★$144
  6. Hotel Saint Clair - Magnificent Mile · 18 nights measured4★$154
  7. Congress Plaza Hotel · 21 nights measured3★$164
  8. Hampton Inn Chicago-Midway Airport · 21 nights measured3★$166
  9. Hotel Felix · 21 nights measured4★$167
  10. Hilton Garden Inn Chicago/Midway Airport · 21 nights measured3★$170
  11. Eurostars Magnificent Mile · 21 nights measured4★$170
  12. Hilton Garden Inn Chicago McCormick Place · 14 nights measured3★$172
  13. Chicago South Loop Hotel · 21 nights measured3★$172
  14. Sonesta ES Suites Chicago Downtown Magnificent Mile Medical · 20 nights measured3★$176
  15. Hotel Lincoln · 15 nights measured4★$176
  16. Claridge House Chicago, Tapestry Collection by Hilton · 19 nights measured4★$177
  17. Hotel Versey Chicago Lincoln Park · 17 nights measured3★$179
  18. Central Loop Hotel · 18 nights measured4★$181
  19. Best Western Chicago Downtown-River North · 20 nights measured3★$182
  20. Home2 Suites By Hilton Chicago McCormick Place · 7 nights measured3★$184
  21. Holiday Inn & Suites Chicago-Downtown by IHG · 19 nights measured3★$184
  22. Hilton Chicago/Oak Lawn · 21 nights measured3★$188
  23. Cambria Hotel Chicago Loop - Theatre District · 16 nights measured4★$191
  24. The Willows Hotel · 21 nights measured3★$191
  25. Chicago Lake Shore Hotel · 21 nights measured3★$192
  26. Hilton Vacation Club Hotel Blake Chicago · 7 nights measured5★$193
  27. SpringHill Suites by Marriott Chicago Chinatown · 17 nights measured3★$196
  28. City Suites Hotel · 21 nights measured3★$197
  29. Hilton Grand Vacations Club Chicago Magnificent Mile · 14 nights measured3★$198
  30. AC Hotel Chicago Downtown · 20 nights measured4★$199
Show the other 113 hotels
  1. Le Meridien Essex Chicago · 21 nights measured4★$203
  2. The Wade · 21 nights measured4★$205
  3. Best Western Grant Park Hotel · 15 nights measured3★$208
  4. Hampton Inn Chicago McCormick Place · 11 nights measured3★$209
  5. Hilton Chicago Magnificent Mile Suites · 21 nights measured3★$209
  6. The Godfrey Hotel Chicago · 21 nights measured4★$210
  7. Club Quarters Hotel Wacker at Michigan, Chicago · 16 nights measured4★$212
  8. River Hotel · 16 nights measured4★$212
  9. Riu Plaza Chicago · 18 nights measured4★$212
  10. Kinzie Hotel · 18 nights measured4★$215
  11. Hilton Garden Inn Chicago Downtown/Magnificent Mile · 17 nights measured3★$216
  12. Holiday Inn Express Chicago - Magnificent Mile by IHG · 20 nights measured3★$216
  13. Best Western Plus Hawthorne Terrace Hotel · 15 nights measured3★$216
  14. The Buckingham Hotel · 15 nights measured3★$218
  15. Arlo Chicago · 21 nights measured4★$220
  16. Hampton Inn Chicago Downtown/Magnificent Mile · 17 nights measured3★$221
  17. Jaslin Hotel · 15 nights measured3★$226
  18. Hampton Inn Chicago North-Loyola Station · 21 nights measured3★$229
  19. ACME Hotel Chicago, Outset Collection by Hilton · 19 nights measured4★$229
  20. The Majestic Hotel · 21 nights measured3★$230
  21. Homewood Suites by Hilton Chicago Downtown - Magnificent Mile · 16 nights measured3★$231
  22. Staypineapple, An Iconic Hotel, The Loop · 21 nights measured4★$231
  23. The Drake Hotel · 13 nights measured4★$232
  24. Crowne Plaza - Chicago West Loop by IHG · 21 nights measured3★$233
  25. Home2 Suites By Hilton Chicago River North · 21 nights measured3★$236
  26. Sable At Navy Pier Chicago, Curio Collection By Hilton · 21 nights measured4★$238
  27. Hyatt House Chicago Medical/University District · 21 nights measured4★$239
  28. Hilton Garden Inn Chicago Downtown Riverwalk · 19 nights measured3★$242
  29. Ivy Boutique Hotel · 21 nights measured4★$246
  30. Pendry Chicago · 20 nights measured4★$249
  31. Hotel 55 Chicago Downtown · 21 nights measured4★$252
  32. Aloft Chicago Mag Mile · 19 nights measured3★$252
  33. Hilton Garden Inn Chicago Downtown South Loop · 17 nights measured3★$262
  34. Hampton Inn & Suites Chicago Medical District Uic · 21 nights measured3★$264
  35. Embassy Suites by Hilton Chicago Downtown Magnificent Mile · 16 nights measured4★$264
  36. The Royal Sonesta Chicago Downtown · 19 nights measured4★$264
  37. Silversmith Hotel Chicago Downtown · 17 nights measured4★$269
  38. Hampton Inn & Suites Chicago-Downtown · 14 nights measured3★$269
  39. Hyatt Place Chicago-South/University Medical Center · 17 nights measured3★$272
  40. Hampton Inn Chicago Downtown/N Loop/Michigan Ave · 15 nights measured3★$279
  41. La Quinta Inn & Suites by Wyndham Chicago Downtown · 19 nights measured3★$284
  42. Hyatt House Chicago West Loop-Fulton Market · 17 nights measured3★$285
  43. Homewood Suites By Hilton Chicago Downtown South Loop · 16 nights measured3★$287
  44. Embassy Suites Chicago - Downtown River North · 19 nights measured3★$287
  45. The Allegro Royal Sonesta Hotel Chicago Loop · 18 nights measured4★$289
  46. Fairfield Inn and Suites Chicago Downtown/ Magnificent Mile · 19 nights measured3★$296
  47. Homewood Suites by Hilton Chicago-Downtown · 18 nights measured3★$297
  48. Sentral Michigan Avenue · 21 nights measured3★$303
  49. citizenM Chicago Downtown · 21 nights measured4★$303
  50. Omni Chicago Hotel · 16 nights measured4★$305
  51. Hyatt Place Chicago Medical/University District · 21 nights measured4★$308
  52. The Royal Sonesta Chicago River North · 13 nights measured4★$309
  53. Canopy By Hilton Chicago Central Loop · 17 nights measured4★$313
  54. Hampton Inn Majestic Chicago Theatre District · 15 nights measured3★$316
  55. Sports Illustrated Resorts Chicago · 18 nights measured4★$318
  56. L7 Chicago by LOTTE · 18 nights measured4★$321
  57. voco Chicago Downtown - Riverwalk by IHG · 20 nights measured3★$326
  58. Fairfield Inn and Suites Chicago Downtown-River North · 20 nights measured3★$327
  59. The Westin Michigan Avenue Chicago · 19 nights measured4★$330
  60. Hyatt Place Chicago River North · 20 nights measured3★$331
  61. Sophy Hyde Park · 16 nights measured4★$331
  62. DoubleTree by Hilton Chicago Magnificent Mile · 17 nights measured4★$331
  63. The Palmer House Hilton · 19 nights measured4★$339
  64. InterContinental Chicago Magnificent Mile by IHG · 18 nights measured4★$342
  65. Hyatt Regency McCormick Place Chicago · 18 nights measured4★$345
  66. Radisson Blu Aqua Hotel, Chicago · 19 nights measured4★$346
  67. Hyatt Place Chicago Wicker Park · 13 nights measured3★$355
  68. Moxy Chicago Downtown · 21 nights measured3★$356
  69. Hotel Chicago Downtown, Autograph Collection · 19 nights measured4★$367
  70. theWit Chicago, a Hilton Hotel · 16 nights measured4★$368
  71. The Robey, Chicago, a Member of Design Hotels · 14 nights measured4★$368
  72. Hyatt Centric Chicago Magnificent Mile · 16 nights measured4★$371
  73. Courtyard by Marriott Chicago Downtown/River North · 18 nights measured3★$377
  74. Residence Inn by Marriott Chicago Downtown Magnificent Mile · 20 nights measured3★$404
  75. Level Chicago - Fulton Market · 21 nights measured5★$412
  76. Hyatt Regency Chicago · 18 nights measured4★$415
  77. The Emily Hotel · 15 nights measured4★$417
  78. Courtyard by Marriott Chicago at Medical District-UIC · 16 nights measured3★$423
  79. Springhill Suites by Marriott Chicago Downtown/ River North · 21 nights measured3★$430
  80. Courtyard Chicago Downtown/Magnificent Mile · 20 nights measured4★$442
  81. Marriott Marquis Chicago · 18 nights measured4★$442
  82. Sofitel Chicago Magnificent Mile · 21 nights measured5★$443
  83. Sheraton Grand Chicago Riverwalk · 19 nights measured4★$443
  84. Chicago Marriott Downtown Magnificent Mile · 17 nights measured4★$444
  85. Residence Inn by Marriott Chicago Downtown / River North · 21 nights measured3★$446
  86. Hampton Inn Chicago West Loop Fulton Market Area · 20 nights measured3★$453
  87. Thompson Chicago, by Hyatt · 20 nights measured4★$456
  88. Hilton Garden Inn- Chicago Central Loop · 19 nights measured3★$457
  89. Hotel EMC2, Autograph Collection · 21 nights measured4★$466
  90. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area · 21 nights measured3★$481
  91. Hyatt Place Chicago/Downtown - The Loop · 20 nights measured3★$530
  92. Aloft by Marriott Chicago Downtown River North · 20 nights measured3★$532
  93. Trump International Hotel & Tower Chicago · 21 nights measured5★$535
  94. Loews Chicago Hotel · 18 nights measured4★$545
  95. Viceroy Chicago · 20 nights measured5★$573
  96. Hyatt Centric The Loop Chicago · 19 nights measured4★$614
  97. LondonHouse Chicago, Curio Collection by Hilton · 20 nights measured4★$616
  98. Residence Inn Chicago Downtown/Loop · 21 nights measured3★$618
  99. The Hoxton, Chicago · 14 nights measured4★$657
  100. The Ritz-Carlton, Chicago · 21 nights measured5★$679
  101. Renaissance Chicago Downtown Hotel · 19 nights measured4★$687
  102. Park Hyatt Chicago · 21 nights measured5★$777
  103. Swissotel Chicago · 16 nights measured4★$781
  104. Nobu Hotel Chicago · 19 nights measured5★$787
  105. The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago · 20 nights measured4★$842
  106. JW Marriott Chicago · 19 nights measured5★$858
  107. The St. Regis Chicago · 21 nights measured5★$905
  108. The Peninsula Chicago · 21 nights measured5★$928
  109. The Langham Chicago · 16 nights measured5★$945
  110. Waldorf Astoria Chicago · 20 nights measured5★$988
  111. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel · 21 nights measured4★$994
  112. Four Seasons Chicago · 20 nights measured5★$1,609
  113. Hotel Zachary, Chicago, a Tribute Portfolio Hotel · 20 nights measured4★$1,959

Recent Chicago deal records

  1. Level Chicago - Fulton Market$1,418 total7 nights from 15 Dec 202664% below · 14 comparable
  2. Hilton Vacation Club Hotel Blake Chicago$1,319 total7 nights from 21 Dec 202663% below · 14 comparable

Watch Chicago

We email you when a month here gets materially cheaper. Nothing else — no digest, no weekly send.

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.