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Local Getaways
Find the best hotels within 350 miles for a spontaneous adventure.
Cincinnati
Cleveland
Unavailable
2 Rooms Left
Solid
DAILY DROP
LEVEL Chicago - Old Town
$423
89%
|
–
Downtown
was on HT
$604
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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Unavailable
Solid
DEAL
Chez Hotel
$143
90%
|
–
Downtown
was on HT
$158
Unavailable
3 Rooms Left
Hip
DEAL
LondonHouse Chicago
$357
97%
|
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Loop
was on HT
$757
Part classic 1920s architecture, part sleek glass tower. All impressive.
Unavailable
2 Rooms Left
Solid
DEAL
Level Chicago - Fulton Market
$315
81%
|
–
Downtown
was on HT
$439
The outdoor pool takes vacay vibes to new heights.
Unavailable
Solid
DEAL
The Chicago Hotel Collection - Magnificent Mile
$158
85%
|
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Magnificent Mile
was on HT
$298
Modern design and bohemian-chic flair flow throughout this vibrant atmosphere.
Unavailable
Hip
DEAL
The Allegro Royal Sonesta Hotel Chicago Loop
$270
90%
|
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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
Basic
Hampton Inn Chicago Orland Park
$140
86%
|
–
West Side
Unavailable
Hip
DEAL
The Hoxton, Chicago
$360
95%
|
–
West Loop
was on HT
$479
This hip London-based brand transformed 3 meatpacking warehouses into a stylish new hotel inspired by the local architecture and galleries.
Unavailable
Solid
DEAL
The Royal Sonesta Chicago River North
$315
94%
|
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River North
Sophisticated and chic, with just enough quirk to keep things cool.
Unavailable
3 Rooms Left
Charming
DEAL
The Buckingham Hotel
$324
90%
|
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Loop
was on HT
$505
Right at the Chicago Stock Exchange in the Financial District. Good thing hard work here gets you serious pampering.
Unavailable
Solid
DEAL
Aloft Chicago Mag Mile
$300
91%
|
–
Downtown
Stellar Mag Mile location puts the city's best eateries and endless shopping on your doorstep.
Unavailable
Luxe
Viceroy Chicago
$389
97%
|
–
Gold Coast
was on HT
$525
It's shimmery and glittering. Makes sense for the Gold Coast locale.
Unavailable
Charming
Hotel Chicago West Loop
$275
81%
|
–
West Loop
was on HT
$340
Fitness room is open 24/7, if all that museum-ing wasn’t enough of a workout for you.
Unavailable
Luxe
Loews Chicago Hotel
$325
96%
|
–
Magnificent Mile
Head to the rooftop lounge for killer drinks and views (especially if it’s a Navy Pier fireworks night!).
Unavailable
Basic
Majestic Hotel
$216
84%
|
–
Lakeview
was on HT
$275
On a quiet residential street, providing a relaxing respite in the bustling city.
Unavailable
2 Rooms Left
Luxe
L7 Chicago by LOTTE
$351
96%
|
–
Loop
The former hat factory on the banks of the Chicago River features newly renovated and richly decorated rooms.
Unavailable
2 Rooms Left
Basic
Level Chicago - River North
$377
95%
|
–
Downtown
You’ll find chic galleries, buzz-worthy restaurants and vibrant nightlife in this hub for arts and entertainment.
Unavailable
Solid
DEAL
Club Quarters Hotel Wacker at Michigan, Chicago
$275
85%
|
–
Loop
Magnificent Mile’s within a half-mile (read: minimal toting of your shopping spoils required).
Unavailable
Solid
Crowne Plaza Chicago Metro Downtown
$299
88%
|
–
Loop
was on HT
$529
Right on Restaurant Row in Greektown. That deserves an emphatic 'opa!'.
Unavailable
Luxe
The Ritz-Carlton, Chicago
$545
97%
|
–
Magnificent Mile
Can’t-be-beat address on the Magnificent Mile (!).
Unavailable
Hip
citizenM Chicago Downtown
$326
95%
|
–
Loop
Free WiFi, so you can brag about your cool trip in real-time.
Unavailable
Hip
DEAL
21c Museum Hotel Chicago
$324
95%
|
–
Downtown
was on HT
$499
This boutique hotel also houses its very own art museum filled with 21st-century pieces from emerging artists.
Unavailable
Luxe
DEAL
The Blackstone, Autograph Collection
$450
88%
|
–
Loop
was on HT
$559
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
Ambassador Chicago
$349
92%
|
–
Gold Coast
was on HT
$438
Sleek, modern and eclectic design welcomes the beautiful people. Now you can be one of them!
Unavailable
Solid
Club Quarters Hotel Central Loop, Chicago
$306
84%
|
–
Loop
Chicago biggies like the Symphony Center & Willis Tower (skydeck is a must!) are within walking distance.
Unavailable
Solid
Holiday Inn Express Chicago Magnificent Mile
$287
–
North Side
was on HT
$342
Free WiFi, so you can brag about your cool trip in real time.
Unavailable
2 Rooms Left
Solid
DEAL
LEVEL Chicago - Old Town
$484
89%
|
–
Downtown
was on HT
$604
Stay fit in the fitness center, or head outside for bocce ball or a game of hoops on the rooftop basketball court.
Unavailable
Basic
Holiday Inn Hotel & Suites Chicago Downtown
$259
73%
|
–
Loop
was on HT
$327
Hit nearby Lou Mitchell’s for breakfast. It’s a Chicago institution and the starting point of Route 66.
Unavailable
Luxe
Waldorf Astoria Chicago
$535
96%
|
–
Downtown
was on HT
$570
Guestrooms with kitted-out bathrooms (ft. a soaker tub + inset flat-screen, natch), wet bars & surround sound are a good time waiting to happen.
Unavailable
Solid
Courtyard by Marriott Chicago at Medical District / UIC
$399
92%
|
–
Downtown
Spot-on location for all things medical campus – near UIC Chicago and Rush. PS: Little Italy dining nearby too(!).
Unavailable
1 Room Left
Solid
DEAL
Embassy Suites by Hilton Chicago North Shore Deerfield
$130
95%
|
–
Deerfield
was on HT
$144
Two-room suites give you plenty of space to stretch out.
More amazing deals in:
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Milwaukee,
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San Francisco,
Los Angeles,
Boston,
Miami Beach,
Washington, DC,
Denver,
and tons more!