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Hotels (189)

B&Bs / Inns (23)

Specialty Lodging (58)

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The Guesthouse Hotel (Chicago, IL) 4.0 of 5
4872 N Clark St, Chicago, IL 60640-4711
The Guesthouse Hotel Slideshow
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$302 - $589 Avg. price/night*
Ollie #1 of 189 hotels in Chicago
  •  Incredible Property! 
  • This hotel is just like having your own pied a terre in a different city... more
  • June 22, 2017
Professional photos | Traveler photos (136)
Travelers' Choice® 2017 Winner Luxury
 
The Langham, Chicago (Chicago, IL) 5.0 of 5
330 North Wabash Avenue, Chicago, IL 60611-3586
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$379 - $880 Avg. price/night*
Ollie #2 of 189 hotels in Chicago
Professional photos | Traveler photos (1056)
Special Price Book Early, up to 15...
Certificate of Excellence
Travelers' Choice® 2017 Winner Luxury
 
The Peninsula Chicago (Chicago, IL) 5.0 of 5
108 E Superior St, at North Michigan Avenue, Chicago, IL 60611-2645
The Peninsula Chicago Slideshow
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$372 - $1,346 Avg. price/night*
Ollie #3 of 189 hotels in Chicago
  •  WOW! 
  • Extraordinary hotel in every aspect. Impeccable service, accommodations... more
  • June 22, 2017
Professional photos | Traveler photos (879)
Special Rate Summer Online Upgrade
1209 W Albion Ave, Chicago, IL 60626-4713
Hampton Inn Chicago North - Loyola Station Slideshow
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$158 - $310 Avg. price/night*
Ollie #4 of 189 hotels in Chicago
Traveler photos (77)
Special Offer Hilton Summer Sale!
120 E. Delaware Pl., Chicago, IL 60611-1443
Four Seasons Hotel Chicago Slideshow
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$322 - $1,213 Avg. price/night*
Ollie #5 of 189 hotels in Chicago
  •  Best hotel in Chicago 
  • From Marius at the door to the perfefection of the creases in my sheets... more
  • June 23, 2017
Professional photos | Traveler photos (892)
Special Offer Advance Purchase Package
21 E. Bellevue Place, Chicago, IL 60611-1174
Thompson Chicago, a Thompson Hotel Slideshow
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$234 - $488 Avg. price/night*
Ollie #6 of 189 hotels in Chicago
  •  Omg... how great! 
  • Recently stayed at the Thompson Chicago and have nothing but great things... more
  • June 22, 2017
Professional photos | Traveler photos (830)
Special Offer Uncover Summer
Conrad Chicago (Chicago, IL) 4.5 of 5
101 E Erie St, Chicago, IL 60611-2812
Conrad Chicago Slideshow
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$278 - $489 Avg. price/night*
Ollie #7 of 189 hotels in Chicago
Professional photos | Traveler photos (112)
Special Offer Hilton Summer Sale!
Park Hyatt Chicago (Chicago, IL) 5.0 of 5
800 N Michigan Ave, on Water Tower Square, Chicago, IL 60611-2105
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$293 - $622 Avg. price/night*
Ollie #8 of 189 hotels in Chicago
Professional photos | Traveler photos (411)
Announcement Festival Season is here!
116 N Jefferson St, Chicago, IL 60661
Hampton Inn Chicago Downtown West Loop Slideshow
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$162 - $336 Avg. price/night*
Ollie #9 of 189 hotels in Chicago
  •  Great Location 
  • A great location in the West Loop near Amtrak, Metra, and the L trains... more
  • June 23, 2017
Traveler photos (91)
Special Offer Hilton Summer Sale!
Kimpton Gray Hotel (Chicago, IL) 4.5 of 5
122 W Monroe St, Chicago, IL 60603-5032
Kimpton Gray Hotel Slideshow
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$198 - $487 Avg. price/night*
Ollie #10 of 189 hotels in Chicago
  •  Perfection  
  • The hotel doesn't miss a beat. As a frequent business traveler it's the... more
  • June 21, 2017
Professional photos | Traveler photos (123)
Special Offer Book Direct: 30% Off!
Loews Chicago Hotel (Chicago, IL) 4.5 of 5
455 N Park Drive, Chicago, IL 60611-5886
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$204 - $466 Avg. price/night*
Ollie #11 of 189 hotels in Chicago
  •  Loews Chicago 
  • Convenient hotel. Top shelf like most Loews. Great views, particularly on... more
  • June 23, 2017
Professional photos | Traveler photos (607)
Special Offer Summer Sale: 20% Off
505 North State Street, Chicago, IL 60654-4803
Kimpton Hotel Palomar Chicago Slideshow
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$214 - $471 Avg. price/night*
Ollie #12 of 189 hotels in Chicago
Professional photos | Traveler photos (1192)
Special Offer Book Direct: Get 30...
The Talbott Hotel (Chicago, IL) 4.0 of 5
20 East Delaware Place, Chicago, IL 60611
The Talbott Hotel Slideshow
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$190 - $501 Avg. price/night*
Ollie #13 of 189 hotels in Chicago
Professional photos | Traveler photos (911)
Special Offer Sips of Summer
Virgin Hotels Chicago (Chicago, IL) 4.5 of 5
203 N Wabash Ave, Chicago, IL 60601-2424
Virgin Hotels Chicago Slideshow
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$196 - $432 Avg. price/night*
Ollie #14 of 189 hotels in Chicago
  •  Trendy Hôtel  
  • It's not really a boutique hotel but more a trendy one like Hard Rock... more
  • June 22, 2017
Professional photos | Traveler photos (990)
Special Offer Perfectly Planned
11 East Walton, Chicago, IL 60611-1412
Waldorf Astoria Chicago Slideshow
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$372 - $705 Avg. price/night*
Ollie #15 of 189 hotels in Chicago
Professional photos | Traveler photos (810)
Special Offer Hilton Summer Sale!
60 W Illinois St, Chicago, IL 60654-4805
Fairfield Inn & Suites Chicago Downtown/River North Slideshow
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$182 - $371 Avg. price/night*
Ollie #16 of 189 hotels in Chicago
  •  No closet or drawers 
  • This is a pleasant hotel with a friendly staff in a great location. The... more
  • June 22, 2017
Professional photos | Traveler photos (334)
Special Offer Rainforest Café Package
The Silversmith Hotel (Chicago, IL) 4.0 of 5
10 S Wabash Ave, Chicago, IL 60603-2801
No photo provided
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$198 - $365 Avg. price/night*
Ollie #17 of 189 hotels in Chicago
Professional photos | Traveler photos (577)
Offers & Announcements Save 10% Off
12 South Michigan Avenue, Chicago, IL 60603
Chicago Athletic Association Hotel Slideshow
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$214 - $595 Avg. price/night*
Ollie #18 of 189 hotels in Chicago
Professional photos | Traveler photos (863)
Special Offer Up To $125 Dining Credit
221 N. Columbus Drive, Chicago, IL 60601-7801
Radisson Blu Aqua Hotel Slideshow
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$217 - $500 Avg. price/night*
Ollie #19 of 189 hotels in Chicago
Professional photos | Traveler photos (1567)
Special Offer Bed & Breakfast for Two
225 N Wabash Avenue, Chicago, IL 60601-2404
Kimpton Hotel Monaco Chicago Slideshow
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$192 - $524 Avg. price/night*
Ollie #20 of 189 hotels in Chicago
  •  Perfect! 
  • Comfy and quiet! Room was just perfect. Just the right size room for a... more
  • June 19, 2017
Professional photos | Traveler photos (1207)
Special Offer Book Direct: 30% Off!

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4.0 of 5 bubbles | 38 Reviews