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Local Getaways
Find the best hotels within 350 miles for a spontaneous adventure.
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Unavailable
3 Rooms Left
Solid
DAILY DROP
LEVEL Chicago - Old Town
$374
89%
|
–
Downtown
was on HT
$545
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
Luxe
DEAL
The Blackstone, Autograph Collection
$120
91%
|
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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
Basic
DEAL
Home2 Suites by Hilton Chicago River North
$102
89%
|
–
Downtown
was on HT
$156
Stellar River North location makes urban exploring a breeze.
Unavailable
Solid
DEAL
Level Chicago - Fulton Market
$144
87%
|
–
Downtown
was on HT
$279
The outdoor pool takes vacay vibes to new heights.
Unavailable
1 Room Left
Solid
The Chicago Hotel Collection - Magnificent Mile
$46
84%
|
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Magnificent Mile
was on HT
$153
Modern design and bohemian-chic flair flow throughout this vibrant atmosphere.
Unavailable
3 Rooms Left
Solid
DEAL
Hilton Garden Inn Chicago McCormick Place
$129
95%
|
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Loop
Polished flair throughout, with soaring ceilings and designery touches. Adjacent to the new Wintrust Arena, if that’s where you’re headed.
Unavailable
Basic
DEAL
Hampton Inn Chicago Orland Park
$110
89%
|
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West Side
Unavailable
Solid
DEAL
River Hotel
$121
86%
|
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Loop
was on HT
$153
Excellent authentic Italian resto onsite with fab deep dish pizza (natch).
Unavailable
Basic
DEAL
St. Clair Hotel - Magnificent Mile
$116
81%
|
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Downtown
was on HT
$170
Modern interiors within a cool old building, ideally situated in the heart of the city, steps from the Magnificent Mile.
Unavailable
Hip
The Allegro Royal Sonesta Hotel Chicago Loop
$137
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
Solid
Aloft Chicago Mag Mile
$139
91%
|
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Downtown
was on HT
$999
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
$270
95%
|
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West Loop
was on HT
$349
This hip London-based brand transformed 3 meatpacking warehouses into a stylish new hotel inspired by the local architecture and galleries.
Unavailable
Charming
Hotel Chicago West Loop
$127
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
2 Rooms Left
Luxe
Pendry Chicago
$192
96%
|
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Loop
was on HT
$280
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
3 Rooms Left
Hip
21c Museum Hotel Chicago
$136
95%
|
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Downtown
was on HT
$156
This boutique hotel also houses its very own art museum filled with 21st-century pieces from emerging artists.
Unavailable
Solid
DEAL
Club Quarters Hotel Wacker at Michigan, Chicago
$121
85%
|
–
Loop
Magnificent Mile’s within a half-mile (read: minimal toting of your shopping spoils required).
Unavailable
Solid
The Royal Sonesta Chicago River North
$162
94%
|
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River North
Sophisticated and chic, with just enough quirk to keep things cool.
Unavailable
1 Room Left
Charming
DEAL
Wicker Park Inn
$208
94%
|
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Wicker Park
was on HT
$229
Drops ya in the heart of a vibrant, trendier-than-thou ‘hood teaming with vintage shopping, cool eateries & hoppin’ nightlife.
Unavailable
Luxe
Viceroy Chicago
$315
97%
|
–
Gold Coast
was on HT
$395
It's shimmery and glittering. Makes sense for the Gold Coast locale.
Unavailable
Solid
Club Quarters Hotel Central Loop, Chicago
$126
85%
|
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Loop
Chicago biggies like the Symphony Center & Willis Tower (skydeck is a must!) are within walking distance.
Unavailable
Luxe
DEAL
The Ritz-Carlton, Chicago
$469
95%
|
–
Magnificent Mile
was on HT
$625
Can’t-be-beat address on the Magnificent Mile (!).
Unavailable
Solid
ACME Hotel Company Chicago
$139
93%
|
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River North
Playful-meets-industrial-chic design with bold, colorful and artistic accents.
Unavailable
Basic
Holiday Inn Hotel & Suites Chicago Downtown
$129
82%
|
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Loop
was on HT
$151
Hit nearby Lou Mitchell’s for breakfast. It’s a Chicago institution and the starting point of Route 66.
Unavailable
Hip
Ambassador Chicago
$229
92%
|
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Gold Coast
Sleek, modern and eclectic design welcomes the beautiful people. Now you can be one of them!
Unavailable
Solid
Courtyard by Marriott Chicago at Medical District / UIC
$159
92%
|
–
Downtown
Spot-on location for all things medical campus – near UIC Chicago and Rush. PS: Little Italy dining nearby too(!).
Unavailable
Solid
Crowne Plaza Chicago Metro Downtown
$159
88%
|
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Loop
was on HT
$174
Right on Restaurant Row in Greektown. That deserves an emphatic 'opa!'.
Unavailable
Solid
Holiday Inn Chicago Mart Plaza River North
$134
96%
|
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River North
was on HT
$149
All rooms are at least 15 stories above the city. Street noise? Nuh-uh.
Unavailable
3 Rooms Left
Solid
DEAL
LEVEL Chicago - Old Town
$428
89%
|
–
Downtown
was on HT
$545
Stay fit in the fitness center, or head outside for bocce ball or a game of hoops on the rooftop basketball court.
Unavailable
Solid
Holiday Inn Express & Suites CHICAGO - OAK FOREST
$119
–
North Side
was on HT
$129
Unavailable
Luxe
Omni Chicago Hotel
$208
90%
|
–
Magnificent Mile
Ideal Mag Mile address just steps from endless shopping & world-class eateries.
Unavailable
Solid
Holiday Inn Express Chicago Magnificent Mile
$164
83%
|
–
North Side
was on HT
$176
Free WiFi, so you can brag about your cool trip in real time.
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Boston,
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Washington, DC,
Denver,
and tons more!