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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 pricesChecked rate: one refundable night, 30 days ahead
  1. Freehand Chicago · 32 nights measured4★$98
  2. The Chicago Hotel Collection River North · 30 nights measured3★$117
  3. Best Western Grant Park Hotel · 23 nights measured3★$161
  4. The Royal Sonesta Chicago River North · 23 nights measured4★$176
  5. Central Loop Hotel · 24 nights measured4★$177
  6. Chicago Lake Shore Hotel · 32 nights measured3★$179
  7. Hampton Inn Chicago-Midway Airport · 32 nights measured3★$182
  8. Best Western Plus Hawthorne Terrace Hotel · 22 nights measured3★$197
  9. Cambria Hotel Chicago Loop - Theatre District · 27 nights measured4★$200
  10. Sonesta ES Suites Chicago Downtown Magnificent Mile Medical · 29 nights measured3★$201
  11. Hampton Inn Chicago Downtown/Magnificent Mile · 28 nights measured3★$204
  12. Jaslin Hotel · 24 nights measured3★$205
  13. Millennium Hotel Knickerbocker Chicago · 32 nights measured4★$206
  14. Hilton Chicago/Oak Lawn · 32 nights measured3★$208
  15. Chicago South Loop Hotel · 32 nights measured3★$213
  16. Hilton Garden Inn Chicago/Midway Airport · 32 nights measured3★$213
  17. Kinzie Hotel · 27 nights measured4★$218
  18. Hotel Saint Clair - Magnificent Mile · 28 nights measured4★$223
  19. Congress Plaza Hotel · 32 nights measured3★$231
  20. Hyatt House Chicago Medical/University District · 32 nights measured4★$242
  21. La Quinta Inn & Suites by Wyndham Chicago Downtown · 30 nights measured3★$246
  22. The Allegro Royal Sonesta Hotel Chicago Loop · 29 nights measured4★$249
  23. AC Hotel Chicago Downtown · 30 nights measured4★$249
  24. The Buckingham Hotel · 21 nights measured3★$252
  25. Home2 Suites By Hilton Chicago McCormick Place · 13 nights measured3★$252
  26. The Whitehall Hotel - BW Premier Collection · 29 nights measured3★$256
  27. Best Western Chicago Downtown-River North · 31 nights measured3★$262
  28. Hotel Felix · 32 nights measured4★$265
  29. Silversmith Hotel Chicago Downtown · 28 nights measured4★$267
  30. Courtyard by Marriott Chicago Downtown/River North · 29 nights measured3★$267
Show the other 113 hotels
  1. Hilton Vacation Club Hotel Blake Chicago · 13 nights measured5★$271
  2. Sable At Navy Pier Chicago, Curio Collection By Hilton · 32 nights measured4★$273
  3. Home2 Suites By Hilton Chicago River North · 32 nights measured3★$278
  4. Hilton Garden Inn Chicago McCormick Place · 21 nights measured3★$280
  5. Hilton Garden Inn Chicago Downtown/Magnificent Mile · 28 nights measured3★$283
  6. Hilton Garden Inn- Chicago Central Loop · 28 nights measured3★$284
  7. City Suites Hotel · 32 nights measured3★$286
  8. Aloft Chicago Mag Mile · 30 nights measured3★$288
  9. Holiday Inn & Suites Chicago-Downtown by IHG · 29 nights measured3★$289
  10. Hampton Inn Chicago McCormick Place · 18 nights measured3★$290
  11. Crowne Plaza - Chicago West Loop by IHG · 32 nights measured3★$296
  12. Club Quarters Hotel Wacker at Michigan, Chicago · 26 nights measured4★$296
  13. Embassy Suites by Hilton Chicago Downtown Magnificent Mile · 27 nights measured4★$297
  14. The Drake Hotel · 19 nights measured4★$297
  15. Arlo Chicago · 32 nights measured4★$298
  16. Hampton Inn & Suites Chicago Medical District Uic · 32 nights measured3★$305
  17. Fairfield Inn and Suites Chicago Downtown/ Magnificent Mile · 30 nights measured3★$306
  18. Hotel Versey Chicago Lincoln Park · 28 nights measured3★$308
  19. Hyatt Place Chicago/Downtown - The Loop · 31 nights measured3★$308
  20. Homewood Suites by Hilton Chicago Downtown - Magnificent Mile · 27 nights measured3★$309
  21. Sports Illustrated Resorts Chicago · 29 nights measured4★$310
  22. Hilton Chicago Magnificent Mile Suites · 32 nights measured3★$312
  23. The Godfrey Hotel Chicago · 32 nights measured4★$317
  24. Claridge House Chicago, Tapestry Collection by Hilton · 30 nights measured4★$320
  25. Homewood Suites by Hilton Chicago-Downtown · 26 nights measured3★$320
  26. Canopy By Hilton Chicago Central Loop · 26 nights measured4★$320
  27. Moxy Chicago Downtown · 32 nights measured3★$323
  28. voco Chicago Downtown - Riverwalk by IHG · 31 nights measured3★$323
  29. Chicago Marriott Downtown Magnificent Mile · 27 nights measured4★$328
  30. Ivy Boutique Hotel · 32 nights measured4★$330
  31. Hotel 55 Chicago Downtown · 32 nights measured4★$330
  32. theWit Chicago, a Hilton Hotel · 23 nights measured4★$331
  33. Homewood Suites By Hilton Chicago Downtown South Loop · 25 nights measured3★$332
  34. Hotel Lincoln · 23 nights measured4★$333
  35. Hampton Inn & Suites Chicago-Downtown · 24 nights measured3★$334
  36. Hyatt House Chicago West Loop-Fulton Market · 27 nights measured3★$334
  37. Warwick Allerton Chicago · 29 nights measured4★$335
  38. The Palmer House Hilton · 30 nights measured4★$339
  39. The Willows Hotel · 32 nights measured3★$340
  40. Residence Inn Chicago Downtown/Loop · 32 nights measured3★$340
  41. InterContinental Chicago Magnificent Mile by IHG · 29 nights measured4★$341
  42. Hampton Inn Chicago Downtown/N Loop/Michigan Ave · 22 nights measured3★$343
  43. Hilton Garden Inn Chicago Downtown South Loop · 26 nights measured3★$343
  44. Hyatt Place Chicago Medical/University District · 32 nights measured4★$344
  45. Embassy Suites Chicago - Downtown River North · 30 nights measured3★$344
  46. ACME Hotel Chicago, Outset Collection by Hilton · 29 nights measured4★$347
  47. Radisson Blu Aqua Hotel, Chicago · 30 nights measured4★$348
  48. The Majestic Hotel · 32 nights measured3★$348
  49. citizenM Chicago Downtown · 32 nights measured4★$349
  50. JW Marriott Chicago · 30 nights measured5★$350
  51. Staypineapple, An Iconic Hotel, The Loop · 32 nights measured4★$351
  52. SpringHill Suites by Marriott Chicago Chinatown · 28 nights measured3★$352
  53. Hilton Garden Inn Chicago Downtown Riverwalk · 30 nights measured3★$360
  54. Fairfield Inn and Suites Chicago Downtown-River North · 31 nights measured3★$361
  55. Courtyard by Marriott Chicago at Medical District-UIC · 25 nights measured3★$369
  56. Hampton Inn Majestic Chicago Theatre District · 22 nights measured3★$370
  57. Omni Chicago Hotel · 25 nights measured4★$372
  58. Springhill Suites by Marriott Chicago Downtown/ River North · 32 nights measured3★$374
  59. Eurostars Magnificent Mile · 32 nights measured4★$375
  60. Le Meridien Essex Chicago · 32 nights measured4★$375
  61. Sentral Michigan Avenue · 32 nights measured3★$376
  62. Hyatt Regency Chicago · 29 nights measured4★$377
  63. The Westin Michigan Avenue Chicago · 29 nights measured4★$379
  64. Aloft by Marriott Chicago Downtown River North · 30 nights measured3★$381
  65. Holiday Inn Express Chicago - Magnificent Mile by IHG · 31 nights measured3★$381
  66. Hyatt Centric The Loop Chicago · 30 nights measured4★$384
  67. Hampton Inn Chicago North-Loyola Station · 31 nights measured3★$384
  68. Hyatt Place Chicago River North · 31 nights measured3★$386
  69. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area · 32 nights measured3★$388
  70. Level Chicago - Fulton Market · 32 nights measured5★$391
  71. Swissotel Chicago · 24 nights measured4★$392
  72. River Hotel · 27 nights measured4★$397
  73. Hampton Inn Chicago West Loop Fulton Market Area · 30 nights measured3★$397
  74. Thompson Chicago, by Hyatt · 31 nights measured4★$400
  75. Residence Inn by Marriott Chicago Downtown / River North · 32 nights measured3★$406
  76. Courtyard Chicago Downtown/Magnificent Mile · 31 nights measured4★$418
  77. Sofitel Chicago Magnificent Mile · 30 nights measured5★$422
  78. LondonHouse Chicago, Curio Collection by Hilton · 31 nights measured4★$428
  79. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel · 31 nights measured4★$430
  80. Hyatt Regency McCormick Place Chicago · 27 nights measured4★$438
  81. The Royal Sonesta Chicago Downtown · 30 nights measured4★$441
  82. Sophy Hyde Park · 27 nights measured4★$443
  83. DoubleTree by Hilton Chicago Magnificent Mile · 28 nights measured4★$450
  84. Hilton Grand Vacations Club Chicago Magnificent Mile · 22 nights measured3★$451
  85. Hyatt Centric Chicago Magnificent Mile · 26 nights measured4★$453
  86. Renaissance Chicago Downtown Hotel · 30 nights measured4★$459
  87. Marriott Marquis Chicago · 28 nights measured4★$462
  88. Residence Inn by Marriott Chicago Downtown Magnificent Mile · 30 nights measured3★$488
  89. The Emily Hotel · 25 nights measured4★$497
  90. Hyatt Place Chicago-South/University Medical Center · 28 nights measured3★$503
  91. Trump International Hotel & Tower Chicago · 32 nights measured5★$505
  92. Sheraton Grand Chicago Riverwalk · 30 nights measured4★$506
  93. Hyatt Place Chicago Wicker Park · 23 nights measured3★$513
  94. Loews Chicago Hotel · 28 nights measured4★$534
  95. The Hoxton, Chicago · 24 nights measured4★$575
  96. Hotel Zachary, Chicago, a Tribute Portfolio Hotel · 29 nights measured4★$586
  97. Pendry Chicago · 31 nights measured4★$588
  98. L7 Chicago by LOTTE · 28 nights measured4★$590
  99. Hotel EMC2, Autograph Collection · 31 nights measured4★$591
  100. Riu Plaza Chicago · 27 nights measured4★$606
  101. Viceroy Chicago · 30 nights measured5★$631
  102. The Ritz-Carlton, Chicago · 29 nights measured5★$645
  103. The Robey, Chicago, a Member of Design Hotels · 25 nights measured4★$654
  104. The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago · 31 nights measured4★$661
  105. Park Hyatt Chicago · 31 nights measured5★$685
  106. Nobu Hotel Chicago · 29 nights measured5★$728
  107. Hotel Chicago Downtown, Autograph Collection · 30 nights measured4★$926
  108. Four Seasons Chicago · 31 nights measured5★$967
  109. The Peninsula Chicago · 32 nights measured5★$1,093
  110. Waldorf Astoria Chicago · 31 nights measured5★$1,149
  111. The St. Regis Chicago · 32 nights measured5★$1,173
  112. The Langham Chicago · 27 nights measured5★$1,312
  113. The Wade · 32 nights measured4★$1,503

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
  3. Freehand Chicago$113 total1 night from 13 Nov 202642% below · 31 nights

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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.