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Local Getaways
Find the best hotels within 350 miles for a spontaneous adventure.
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Unavailable
1 Room Left
Solid
DAILY DROP
LEVEL Chicago - Old Town
$203
89%
|
–
Downtown
was on HT
$691
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
$99
89%
|
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Downtown
was on HT
$141
Unavailable
3 Rooms Left
Hip
DEAL
LondonHouse Chicago
$229
97%
|
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Loop
was on HT
$659
Part classic 1920s architecture, part sleek glass tower. All impressive.
Unavailable
2 Rooms Left
Solid
DEAL
Homewood Suites by Hilton Chicago Downtown
$144
97%
|
–
Downtown
was on HT
$179
Apartment-style suites in the heart of River North (no real estate agent required).
Unavailable
Hip
DEAL
The Allegro Royal Sonesta Hotel Chicago Loop
$160
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
1 Room Left
Basic
DEAL
Level Chicago - River North
$208
95%
|
–
Downtown
You’ll find chic galleries, buzz-worthy restaurants and vibrant nightlife in this hub for arts and entertainment.
Unavailable
2 Rooms Left
Charming
DEAL
The Buckingham Hotel
$176
90%
|
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Loop
was on HT
$351
Right at the Chicago Stock Exchange in the Financial District. Good thing hard work here gets you serious pampering.
Unavailable
Solid
DEAL
The Royal Sonesta Chicago River North
$192
94%
|
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River North
Sophisticated and chic, with just enough quirk to keep things cool.
Unavailable
1 Room Left
Solid
DEAL
The Chicago Hotel Collection - Magnificent Mile
$98
85%
|
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Magnificent Mile
was on HT
$267
Modern design and bohemian-chic flair flow throughout this vibrant atmosphere.
Unavailable
Basic
DEAL
Hampton Inn Chicago Orland Park
$140
86%
|
–
West Side
Unavailable
Solid
DEAL
Aloft Chicago Mag Mile
$179
91%
|
–
Downtown
was on HT
$259
Stellar Mag Mile location puts the city's best eateries and endless shopping on your doorstep.
Unavailable
Hip
DEAL
The Hoxton, Chicago
$315
95%
|
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West Loop
was on HT
$429
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
$240
89%
|
–
Loop
was on HT
$429
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
$189
95%
|
–
Downtown
was on HT
$249
This boutique hotel also houses its very own art museum filled with 21st-century pieces from emerging artists.
Unavailable
Luxe
DEAL
L7 Chicago by LOTTE
$261
96%
|
–
Loop
The former hat factory on the banks of the Chicago River features newly renovated and richly decorated rooms.
Unavailable
Luxe
DEAL
The Ritz-Carlton, Chicago
$492
97%
|
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Magnificent Mile
was on HT
$655
Can’t-be-beat address on the Magnificent Mile (!).
Unavailable
Basic
Sonesta Simply Suites Chicago Waukegan
$91
79%
|
–
Downtown
Suite-style rooms offer up max 'home away from home' vibes.
Unavailable
Solid
DEAL
Holiday Inn Express Chicago Magnificent Mile
$164
–
North Side
was on HT
$219
Free WiFi, so you can brag about your cool trip in real time.
Unavailable
Hip
citizenM Chicago Downtown
$254
95%
|
–
Loop
Free WiFi, so you can brag about your cool trip in real-time.
Unavailable
2 Rooms Left
Luxe
Viceroy Chicago
$425
97%
|
–
Gold Coast
was on HT
$795
It's shimmery and glittering. Makes sense for the Gold Coast locale.
Unavailable
Solid
Hilton Garden Inn Chicago McCormick Place
$239
95%
|
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Loop
was on HT
$314
Polished flair throughout, with soaring ceilings and designery touches. Adjacent to the new Wintrust Arena, if that’s where you’re headed.
Unavailable
Luxe
Loews Chicago Hotel
$309
96%
|
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Magnificent Mile
Head to the rooftop lounge for killer drinks and views (especially if it’s a Navy Pier fireworks night!).
Unavailable
1 Room Left
Basic
Majestic Hotel
$225
84%
|
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Lakeview
was on HT
$275
On a quiet residential street, providing a relaxing respite in the bustling city.
Unavailable
Solid
Level Chicago - Fulton Market
$369
80%
|
–
Downtown
was on HT
$425
The outdoor pool takes vacay vibes to new heights.
Unavailable
1 Room Left
Solid
DEAL
LEVEL Chicago - Old Town
$232
89%
|
–
Downtown
was on HT
$691
Stay fit in the fitness center, or head outside for bocce ball or a game of hoops on the rooftop basketball court.
Unavailable
1 Room Left
Basic
DEAL
The Chicago Hotel Collection - River North
$85
67%
|
–
Downtown
was on HT
$259
Trendy location among the local Near North-ers with easy access to all our favorite downtown haunts.
Unavailable
Solid
Crowne Plaza Chicago Metro Downtown
$244
88%
|
–
Loop
was on HT
$264
Right on Restaurant Row in Greektown. That deserves an emphatic 'opa!'.
Unavailable
Hip
Ambassador Chicago
$276
92%
|
–
Gold Coast
was on HT
$350
Sleek, modern and eclectic design welcomes the beautiful people. Now you can be one of them!
Unavailable
1 Room Left
Basic
St. Clair Hotel - Magnificent Mile
$179
81%
|
–
Downtown
was on HT
$256
Modern interiors within a cool old building, ideally situated in the heart of the city, steps from the Magnificent Mile.
Unavailable
2 Rooms Left
Solid
Club Quarters Hotel Wacker at Michigan, Chicago
$235
85%
|
–
Loop
Magnificent Mile’s within a half-mile (read: minimal toting of your shopping spoils required).
Unavailable
Solid
Courtyard by Marriott Chicago at Medical District / UIC
$279
92%
|
–
Downtown
Spot-on location for all things medical campus – near UIC Chicago and Rush. PS: Little Italy dining nearby too(!).
More amazing deals in:
New York City,
Milwaukee,
Las Vegas - Strip,
San Francisco,
Los Angeles,
Boston,
Miami Beach,
Washington, DC,
Denver,
and tons more!