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Hip
DAILY DROP
The Allegro Royal Sonesta Hotel Chicago Loop
$252
$159
90%
|
–
Loop
per night
Includes fees
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.
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Unavailable
Basic
DEAL
Hampton Inn Chicago Orland Park
$130
$118
96%
|
–
West Side
per night
Includes fees
Unavailable
Hip
DEAL
Hyatt Centric The Loop Chicago
$187
$169
96%
|
–
Loop
per night
Includes fees
Loop location means you're steps from the bustling Financial District and (far bustlier) Theater District.
Unavailable
Hip
The Allegro Royal Sonesta Hotel Chicago Loop
$238
$202
90%
|
–
Loop
per night
Includes fees
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
Luxe
Loews Chicago Hotel
$357
$231
96%
|
–
Magnificent Mile
per night
Includes fees
Head to the rooftop lounge for killer drinks and views (especially if it’s a Navy Pier fireworks night!).
Unavailable
Solid
Hotel Chicago West Loop, Sure Stay Collection By Best Western
$199
$164
82%
|
–
North Side
per night
Includes taxes and fees
Bring your furry friends along for the ride. This place is pet friendly.
Unavailable
Solid
DEAL
The Buckingham Hotel
$174
91%
|
–
Loop
per night
Includes fees
Right at the Chicago Stock Exchange in the Financial District. Good thing hard work here gets you serious pampering.
Unavailable
3 Rooms Left
Hip
DEAL
The Hoxton, Chicago
$306
$230
95%
|
–
West Loop
per night
Includes fees
This hip London-based brand transformed 3 meatpacking warehouses into a stylish new hotel inspired by the local architecture and galleries.
Unavailable
Luxe
DEAL
The Blackstone, Autograph Collection
$271
$231
92%
|
–
Loop
per night
Includes fees
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
1 Room Left
Charming
DEAL
Wicker Park Inn
$228
$194
94%
|
–
Wicker Park
per night
Includes fees
Drops ya in the heart of a vibrant, trendier-than-thou ‘hood teaming with vintage shopping, cool eateries & hoppin’ nightlife.
Unavailable
Luxe
DEAL
Pendry Chicago
$379
$302
96%
|
–
Loop
per night
Includes fees
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
Solid
Hampton Inn & Suites Chicago Downtown
$203
$178
89%
|
–
Downtown
per night
Includes fees
Killer River North location by the Mag Mile and Riverwalk.
Unavailable
Solid
DEAL
Club Quarters Hotel Wacker at Michigan, Chicago
$158
85%
|
–
Loop
per night
Includes fees
Magnificent Mile’s within a half-mile (read: minimal toting of your shopping spoils required).
Unavailable
Solid
DEAL
Aloft Chicago Mag Mile
$301
$207
91%
|
–
Downtown
per night
Includes fees
Stellar Mag Mile location puts the city's best eateries and endless shopping on your doorstep.
Unavailable
3 Rooms Left
Charming
The Guesthouse Hotel
$259
95%
|
–
Andersonville
per night
Includes fees
Apartment-style living at its finest with updated amenities and space galore.
Unavailable
Solid
DEAL
River Hotel
$203
$158
86%
|
–
Loop
per night
Includes fees
Excellent authentic Italian resto onsite with fab deep dish pizza (natch).
Unavailable
3 Rooms Left
Solid
DEAL
Millennium Knickerbocker Hotel Chicago
$175
88%
|
–
Gold Coast
per night
Includes taxes and fees
We love a storied past! 1927 building has housed everyone from JFK to The Rolling Stones (and a penthouse floor casino run by Al Capone’s brother).
Unavailable
Solid
ACME Hotel Company Chicago
$258
$211
93%
|
–
River North
per night
Includes taxes and fees
Playful-meets-industrial-chic design with bold, colorful and artistic accents.
Unavailable
Solid
The Royal Sonesta Chicago River North
$256
94%
|
–
River North
per night
Includes fees
Sophisticated and chic, with just enough quirk to keep things cool.
Unavailable
Luxe
Viceroy Chicago
$405
97%
|
–
Gold Coast
per night
Includes fees
It's shimmery and glittering. Makes sense for the Gold Coast locale.
Unavailable
1 Room Left
Solid
DEAL
Level Chicago - Fulton Market
$615
$331
91%
|
–
Downtown
per night
Includes fees
The outdoor pool takes vacay vibes to new heights.
Unavailable
Hip
DEAL
21c Museum Hotel Chicago
$245
95%
|
–
Downtown
per night
Includes fees
This boutique hotel also houses its very own art museum filled with 21st-century pieces from emerging artists.
Unavailable
Solid
Hilton Chicago Mag Mile Suites
$199
$189
90%
|
–
Downtown
per night
Includes fees
Fab location, just off the Mag Mile, adjacent to the famed John Hancock building.
Unavailable
3 Rooms Left
Hip
Freehand Chicago
$207
$177
83%
|
–
River North
per night
Includes fees
Style in this 20s-era gem is trendy in a laid-back kinda way. And it’s perfectly placed in a venture-worthy boutique-and-gallery-dotted ‘hood.
Unavailable
Hip
DEAL
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
$306
$230
83%
|
–
Loop
per night
Includes fees
Sip signature cocktails at MSC, a stylish bar where guests and locals gather for great conversation and an inviting atmosphere.
Unavailable
Solid
Hilton Garden Inn Chicago McCormick Place
$299
$249
95%
|
–
Loop
per night
Includes fees
Polished flair throughout, with soaring ceilings and designery touches. Adjacent to the new Wintrust Arena, if that’s where you’re headed.
Unavailable
Solid
Club Quarters Hotel Central Loop, Chicago
$171
85%
|
–
Loop
per night
Includes fees
Chicago biggies like the Symphony Center & Willis Tower (skydeck is a must!) are within walking distance.
Unavailable
1 Room Left
Basic
Level Chicago - River North
$429
$360
93%
|
–
Downtown
per night
Includes fees
You’ll find chic galleries, buzz-worthy restaurants and vibrant nightlife in this hub for arts and entertainment.
Unavailable
Luxe
The Ritz-Carlton, Chicago
$625
95%
|
–
Magnificent Mile
per night
Includes fees
Can’t-be-beat address on the Magnificent Mile (!).
Unavailable
Luxe
Sofitel Chicago Magnificent Mile
$405
$335
96%
|
–
Gold Coast
per night
Includes taxes and fees
Walking distance to the Magnificent Mile? Check. Lakefront trail? Check. Public transportation? Check.
Unavailable
1 Room Left
Solid
DEAL
LEVEL Chicago - Old Town
$432
$355
88%
|
–
Downtown
per night
Includes fees
Stay fit in the fitness center, or head outside for bocce ball or a game of hoops on the rooftop basketball court.
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