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Unavailable
Solid
DAILY DROP
The Chicago Hotel Collection - Magnificent Mile
$86
86%
|
–
Magnificent Mile
was on HT
$199
Modern design and bohemian-chic flair flow throughout this vibrant atmosphere.
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Unavailable
Luxe
DEAL
The Blackstone, Autograph Collection
$126
89%
|
–
Loop
was on HT
$199
There’s a reason it’s been voted one of the best hotels in the city – everything is top-notch, from the views, artwork & modern décor to the nostalgic cocktails.
Unavailable
Hip
DEAL
21c Museum Hotel Chicago
$120
95%
|
–
Downtown
was on HT
$133
This boutique hotel also houses its very own art museum filled with 21st-century pieces from emerging artists.
Unavailable
1 Room Left
Charming
DEAL
Wicker Park Inn
$124
94%
|
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Wicker Park
was on HT
$145
Drops ya in the heart of a vibrant, trendier-than-thou ‘hood teaming with vintage shopping, cool eateries & hoppin’ nightlife.
Unavailable
Hip
DEAL
The Allegro Royal Sonesta Hotel Chicago Loop
$122
90%
|
–
Loop
A historic gem in the heart of Chicago’s downtown Theatre District, this boutique haven boasts lavish theatrics all its own with its elegant hobnobbing and glamour.
Unavailable
Solid
DEAL
Aloft Chicago Mag Mile
$119
90%
|
–
Downtown
was on HT
$139
Stellar Mag Mile location puts the city's best eateries and endless shopping on your doorstep.
Unavailable
1 Room Left
Hip
DEAL
The Hoxton, Chicago
$171
95%
|
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West Loop
was on HT
$259
This hip London-based brand transformed 3 meatpacking warehouses into a stylish new hotel inspired by the local architecture and galleries.
Unavailable
2 Rooms Left
Charming
DEAL
The Buckingham Hotel
$126
90%
|
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Loop
was on HT
$209
Right at the Chicago Stock Exchange in the Financial District. Good thing hard work here gets you serious pampering.
Unavailable
Basic
DEAL
Level Chicago - River North
$203
94%
|
–
Downtown
You’ll find chic galleries, buzz-worthy restaurants and vibrant nightlife in this hub for arts and entertainment.
Unavailable
Solid
The Royal Sonesta Chicago River North
$149
94%
|
–
River North
Sophisticated and chic, with just enough quirk to keep things cool.
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2 Rooms Left
Charming
The Publishing House Bed & Breakfast
$165
99%
|
–
West Loop
Formerly the Free Methodist Publishing House, it’s no longer free. Or Methodist. Or a Publishing House. (It is, however, a great place for reading, so bring books!)
Unavailable
Solid
DEAL
The Chicago Hotel Collection - Magnificent Mile
$110
86%
|
–
Magnificent Mile
was on HT
$199
Modern design and bohemian-chic flair flow throughout this vibrant atmosphere.
Unavailable
Luxe
DEAL
Loews Chicago Hotel
$162
96%
|
–
Magnificent Mile
Head to the rooftop lounge for killer drinks and views (especially if it’s a Navy Pier fireworks night!).
Unavailable
Basic
Hampton Inn Chicago Orland Park
$129
75%
|
–
West Side
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Hip
citizenM Chicago Downtown
$139
95%
|
–
Loop
Free WiFi, so you can brag about your cool trip in real-time.
Unavailable
2 Rooms Left
Luxe
DEAL
The Ritz-Carlton, Chicago
$318
98%
|
–
Magnificent Mile
was on HT
$339
Can’t-be-beat address on the Magnificent Mile (!).
Unavailable
Luxe
Pendry Chicago
$265
97%
|
–
Loop
Bar Pendry's a loungey spot for a late-night glass of wine. Pro tip: seasonal rooftop bar's a must-do in the warmer months.
Unavailable
Luxe
Viceroy Chicago
$295
97%
|
–
Gold Coast
It's shimmery and glittering. Makes sense for the Gold Coast locale.
Unavailable
Charming
Hotel Chicago West Loop
$153
81%
|
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West Loop
Fitness room is open 24/7, if all that museum-ing wasn’t enough of a workout for you.
Unavailable
Basic
Majestic Hotel
$108
84%
|
–
Lakeview
was on HT
$118
On a quiet residential street, providing a relaxing respite in the bustling city.
Unavailable
Solid
Club Quarters Hotel Central Loop, Chicago
$108
84%
|
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Loop
Chicago biggies like the Symphony Center & Willis Tower (skydeck is a must!) are within walking distance.
Unavailable
Hip
Ambassador Chicago
$139
92%
|
–
Gold Coast
Sleek, modern and eclectic design welcomes the beautiful people. Now you can be one of them!
Unavailable
Solid
DEAL
Level Chicago - Fulton Market
$225
80%
|
–
Downtown
was on HT
$299
The outdoor pool takes vacay vibes to new heights.
Unavailable
1 Room Left
Charming
House 5863
$188
93%
|
–
Edgewater
was on HT
$233
Urban-contemporary style and sleek, arty shared living room – this is definitely not your grandma’s B&B.
Unavailable
3 Rooms Left
Basic
DEAL
The Chicago Hotel Collection - River North
$73
68%
|
–
Downtown
was on HT
$113
Trendy location among the local Near North-ers with easy access to all our favorite downtown haunts.
Unavailable
Luxe
DEAL
Omni Chicago Hotel
$172
90%
|
–
Magnificent Mile
was on HT
$219
Ideal Mag Mile address just steps from endless shopping & world-class eateries.
Unavailable
Solid
Crowne Plaza Chicago Metro Downtown
$169
88%
|
–
Loop
was on HT
$188
Right on Restaurant Row in Greektown. That deserves an emphatic 'opa!'.
Unavailable
1 Room Left
Solid
DEAL
LEVEL Chicago - Old Town
$248
90%
|
–
Downtown
was on HT
$319
Stay fit in the fitness center, or head outside for bocce ball or a game of hoops on the rooftop basketball court.
Unavailable
2 Rooms Left
Basic
DEAL
St. Clair Hotel - Magnificent Mile
$136
81%
|
–
Downtown
was on HT
$247
Modern interiors within a cool old building, ideally situated in the heart of the city, steps from the Magnificent Mile.
Unavailable
Basic
Holiday Inn Hotel & Suites Chicago Downtown
$141
72%
|
–
Loop
was on HT
$156
Hit nearby Lou Mitchell’s for breakfast. It’s a Chicago institution and the starting point of Route 66.
Unavailable
Solid
Holiday Inn Express Chicago Magnificent Mile
$159
–
North Side
Free WiFi, so you can brag about your cool trip in real time.
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