| 1 | Londonhouse Chicago, Curio Collection By Hilton | 57k | 721 | Chicago, United States | $$$$ |
| 2 | The Palmer House Hilton | 44k | 903 | Chicago, United States | $$$$ |
| 3 | The Langham Chicago | 31k | 341 | Chicago, United States | $$$$ |
| 4 | Trump International Hotel & Tower Chicago | 29k | 1134 | Chicago, United States | $$$$ |
| 5 | Hilton Chicago | 28k | 997 | Chicago, United States | $$$$ |
| 6 | Riu Plaza Chicago | 25k | 8568 | Chicago, United States | $$$$ |
| 7 | The St. Regis Chicago | 23k | 55 | Chicago, United States | $$$$ |
| 8 | The Royal Sonesta Chicago River North | 23k | 1327 | Chicago, United States | $$$$ |
| 9 | Nobu Hotel Chicago | 23k | 388 | Chicago, United States | $$$$ |
| 10 | Four Seasons Chicago | 22k | 129 | Chicago, United States | $$$$ |
| 11 | Sheraton Grand Chicago Riverwalk | 22k | 834 | Chicago, United States | $$$$ |
| 12 | Radisson Blu Aqua Hotel, Chicago | 19k | 1409 | Chicago, United States | $$$$ |
| 13 | Intercontinental Chicago Magnificent Mile By Ihg | 19k | 307 | Chicago, United States | $$$$ |
| 14 | Congress Plaza Hotel Chicago | 19k | 4471 | Chicago, United States | $$$$ |
| 15 | Viceroy Chicago | 18k | 827 | Chicago, United States | $$$$ |
| 16 | Citizenm Chicago Downtown | 17k | 3035 | Chicago, United States | $$$$ |
| 17 | The Drake Hotel | 17k | 643 | Chicago, United States | $$$$ |
| 18 | Chicago Athletic Association, Part Of Hyatt | 16k | 211 | Chicago, United States | $$$$ |
| 19 | Pendry Chicago | 16k | 524 | Chicago, United States | $$$$ |
| 20 | Fairmont Chicago Millennium Park | 16k | 404 | Chicago, United States | $$$$ |
| 21 | Swissotel Chicago | 16k | 991 | Chicago, United States | $$$$ |
| 22 | The Wade | 15k | 1654 | Chicago, United States | $$$$ |
| 23 | Marriott Marquis Chicago | 15k | 338 | Chicago, United States | $$$$ |
| 24 | The Royal Sonesta Chicago Downtown | 15k | 1540 | Chicago, United States | $$$$ |
| 25 | The Peninsula Chicago | 15k | 222 | Chicago, United States | $$$$ |
| 26 | Sable At Navy Pier Chicago, Curio Collection By Hilton | 14k | 878 | Chicago, United States | $$$$ |
| 27 | Thewit Chicago, A Hilton Hotel | 14k | 403 | Chicago, United States | $$$$ |
| 28 | Hyatt Regency Chicago | 13k | 1451 | Chicago, United States | $$$$ |
| 29 | Jw Marriott Chicago | 13k | 188 | Chicago, United States | $$$$ |
| 30 | Hyatt Regency Mccormick Place Chicago | 13k | 1004 | Chicago, United States | $$$$ |
| 31 | Waldorf Astoria Chicago | 13k | 140 | Chicago, United States | $$$$ |
| 32 | The Gwen, A Luxury Collection Hotel, Michigan Avenue Chicago | 13k | 72 | Chicago, United States | $$$$ |
| 33 | Sports Illustrated Resorts Chicago | 12k | 1395 | Chicago, United States | $$$$ |
| 34 | Freehand Chicago | 12k | 2712 | Chicago, United States | $$$$ |
| 35 | The Ritz-Carlton, Chicago | 12k | 53 | Chicago, United States | $$$$ |
| 36 | Loews Chicago Hotel | 11k | 1128 | Chicago, United States | $$$$ |
| 37 | Hyatt Centric Chicago Magnificent Mile | 10k | 344 | Chicago, United States | $$$$ |
| 38 | Thompson Chicago, By Hyatt | 10k | 311 | Chicago, United States | $$$$ |
| 39 | The Rivvy, Chicago Downtown, A Tribute Portfolio Hotel | 10k | 454 | Chicago, United States | $$$$ |
| 40 | Sofitel Chicago Magnificent Mile | 9k | 1112 | Chicago, United States | $$$$ |
| 41 | Hotel Lincoln | 9k | 420 | Chicago, United States | $$$$ |
| 42 | The Hoxton, Chicago | 9k | 227 | Chicago, United States | $$$$ |
| 43 | Chicago Marriott Downtown Magnificent Mile | 9k | 370 | Chicago, United States | $$$$ |
| 44 | The Godfrey Hotel Chicago | 9k | 764 | Chicago, United States | $$$$ |
| 45 | Omni Chicago Hotel | 9k | 651 | Chicago, United States | $$$$ |
| 46 | Kimpton Gray Hotel Chicago By Ihg | 8k | 171 | Chicago, United States | $$$$ |
| 47 | Cambria Hotel Chicago Loop - Theatre District | 8k | 1246 | Chicago, United States | $$$$ |
| 48 | Embassy Suites Chicago - Downtown River North | 8k | 3514 | Chicago, United States | $$$$ |
| 49 | The Blackstone, Autograph Collection | 8k | 164 | Chicago, United States | $$$$ |
| 50 | Aloft By Marriott Chicago Downtown River North | 8k | 364 | Chicago, United States | $$$$ |
| 51 | Aloft By Marriott Chicago Mag Mile | 8k | 2516 | Chicago, United States | $$$$ |
| 52 | Renaissance Chicago Downtown Hotel | 7k | 272 | Chicago, United States | $$$$ |
| 53 | Warwick Allerton Chicago | 7k | 5274 | Chicago, United States | $$$$ |
| 54 | Hilton Chicago Magnificent Mile Suites | 7k | 1209 | Chicago, United States | $$$$ |
| 55 | Hilton Garden Inn Chicago Downtown/Magnificent Mile | 7k | 4000 | Chicago, United States | $$$$ |
| 56 | The Lasalle Chicago, Autograph Collection | 7k | 120 | Chicago, United States | $$$$ |
| 57 | Ambassador Chicago, Part Of Jdv By Hyatt | 7k | 503 | Chicago, United States | $$$$ |
| 58 | Park Hyatt Chicago | 7k | 90 | Chicago, United States | $$$$ |
| 59 | Moxy Chicago Downtown | 7k | 378 | Chicago, United States | $$$$ |
| 60 | Hotel Zachary, Chicago, A Tribute Portfolio Hotel | 7k | 193 | Chicago, United States | $$$$ |
| 61 | The Westin Michigan Avenue Chicago | 7k | 329 | Chicago, United States | $$$$ |
| 62 | Hotel Emc2, Autograph Collection | 6k | 261 | Chicago, United States | $$$$ |
| 63 | Hi Chicago Hostel | 6k | 9737 | Chicago, United States | $$$$ |
| 64 | Doubletree By Hilton Chicago Magnificent Mile | 6k | 1127 | Chicago, United States | $$$$ |
| 65 | Embassy Suites By Hilton Chicago Downtown Magnificent Mile | 6k | 1525 | Chicago, United States | $$$$ |
| 66 | Courtyard Chicago Downtown/Magnificent Mile | 6k | 541 | Chicago, United States | $$$$ |
| 67 | The Westin Chicago River North | 6k | 124 | Chicago, United States | $$$$ |
| 68 | Hyatt Place Chicago River North | 6k | 1233 | Chicago, United States | $$$$ |
| 69 | Arlo Chicago | 6k | 1768 | Chicago, United States | $$$$ |
| 70 | Voco Chicago Downtown - Riverwalk By Ihg | 6k | 458 | Chicago, United States | $$$$ |
| 71 | Canopy By Hilton Chicago Central Loop | 6k | 287 | Chicago, United States | $$$$ |
| 72 | Le Meridien Essex Chicago | 6k | 375 | Chicago, United States | $$$$ |
| 73 | Hyatt Centric The Loop Chicago | 6k | 995 | Chicago, United States | $$$$ |
| 74 | Eurostars Magnificent Mile | 6k | 2203 | Chicago, United States | $$$$ |
| 75 | The Robey, Chicago, A Member Of Design Hotels | 5k | 217 | Chicago, United States | $$$$ |
| 76 | Claridge House Chicago, Tapestry Collection By Hilton | 5k | 539 | Chicago, United States | $$$$ |
| 77 | Hyatt Place Chicago/Downtown - The Loop | 5k | 1886 | Chicago, United States | $$$$ |
| 78 | Hotel Felix | 5k | 1570 | Chicago, United States | $$$$ |
| 79 | Found Hotels, Chicago, Series By Marriott | 5k | 518 | Chicago, United States | $$$$ |
| 80 | Hotel Chicago Downtown, Autograph Collection | 5k | 267 | Chicago, United States | $$$$ |
| 81 | Sentral Michigan Avenue | 5k | 1837 | Chicago, United States | $$$$ |
| 82 | The Talbott, Autograph Collection | 5k | 33 | Chicago, United States | $$$$ |
| 83 | Hilton Vacation Club Hotel Blake Chicago | 5k | 1748 | Chicago, United States | $$$$ |
| 84 | The Chicago Hotel Collection Magnificent Mile | 5k | 1476 | Chicago, United States | $$$$ |
| 85 | Kinzie Hotel | 5k | 1370 | Chicago, United States | $$$$ |
| 86 | Millennium Hotel Knickerbocker Chicago | 5k | 1230 | Chicago, United States | $$$$ |
| 87 | Staypineapple, An Iconic Hotel, The Loop | 5k | 768 | Chicago, United States | $$$$ |
| 88 | River Hotel | 4k | 7944 | Chicago, United States | $$$$ |
| 89 | The Midland Hotel, Chicago, A Tribute Portfolio Hotel | 4k | 297 | Chicago, United States | $$$$ |
| 90 | The Hotel & Athletic Club At Midtown | 4k | 126 | Chicago, United States | $$$$ |
| 91 | L7 Chicago By Lotte | 4k | 2432 | Chicago, United States | $$$$ |
| 92 | Hampton Inn Chicago Downtown/Magnificent Mile | 4k | 516 | Chicago, United States | $$$$ |
| 93 | Best Western Chicago Downtown-River North | 4k | 1905 | Chicago, United States | $$$$ |
| 94 | Hyatt House Chicago West Loop-Fulton Market | 4k | 512 | Chicago, United States | $$$$ |
| 95 | Crowne Plaza - Chicago West Loop By Ihg | 4k | 632 | Chicago, United States | $$$$ |
| 96 | La Quinta Inn & Suites By Wyndham Chicago Downtown | 4k | 3745 | Chicago, United States | $$$$ |
| 97 | Hyatt Place Chicago Wicker Park | 4k | 418 | Chicago, United States | $$$$ |
| 98 | Hilton Garden Inn Chicago Mccormick Place | 4k | 354 | Chicago, United States | $$$$ |
| 99 | Residence Inn By Marriott Chicago Downtown/Loop | 4k | 479 | Chicago, United States | $$$$ |
| 100 | Ivy Boutique Hotel (Adults Only) | 4k | 1308 | Chicago, United States | $$$$ |