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Local Getaways
Find the best hotels within 350 miles for a spontaneous adventure.
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Chicago
Unavailable
3 Rooms Left
Solid
DAILY DROP
Level Chicago - Fulton Market
$182
90%
|
–
Downtown
was on HT
$279
The outdoor pool takes vacay vibes to new heights.
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Unavailable
Hip
DEAL
Hyatt Centric The Loop Chicago
$112
95%
|
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Loop
was on HT
$139
Loop location means you're steps from the bustling Financial District and (far bustlier) Theater District.
Unavailable
Solid
DEAL
Hyatt House Chicago - Medical / University District
$112
95%
|
–
West Side
was on HT
$239
Smart, stylish digs in the masssssive, architecturally impressive former Cook County Hospital building. (It’s a stunner!)
Unavailable
Hip
DEAL
The Allegro Royal Sonesta Hotel Chicago Loop
$116
90%
|
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Loop
was on HT
$161
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
Solid
DEAL
The Buckingham Hotel
$128
91%
|
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Loop
was on HT
$241
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
$152
94%
|
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River North
was on HT
$231
Sophisticated and chic, with just enough quirk to keep things cool.
Unavailable
1 Room Left
Basic
DEAL
Level Chicago - River North
$189
93%
|
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Downtown
was on HT
$229
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
$89
85%
|
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Loop
was on HT
$160
Magnificent Mile’s within a half-mile (read: minimal toting of your shopping spoils required).
Unavailable
Solid
DEAL
River Hotel
$89
86%
|
–
Loop
was on HT
$162
Excellent authentic Italian resto onsite with fab deep dish pizza (natch).
Unavailable
Hip
The Hoxton, Chicago
$306
95%
|
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West Loop
was on HT
$599
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
$180
92%
|
–
Loop
was on HT
$299
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
Hampton Inn Chicago Orland Park
$144
94%
|
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West Side
Unavailable
1 Room Left
Solid
Millennium Knickerbocker Hotel Chicago
$121
88%
|
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Gold Coast
was on HT
$254
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
Hotel Chicago West Loop, Sure Stay Collection By Best Western
$109
–
North Side
was on HT
$129
Bring your furry friends along for the ride. This place is pet friendly.
Unavailable
Luxe
DEAL
Pendry Chicago
$255
96%
|
–
Loop
was on HT
$310
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
Hilton Garden Inn Chicago McCormick Place
$149
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
Luxe
Viceroy Chicago
$345
97%
|
–
Gold Coast
was on HT
$359
It's shimmery and glittering. Makes sense for the Gold Coast locale.
Unavailable
Luxe
DEAL
L7 Chicago by LOTTE
$189
96%
|
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Loop
was on HT
$289
The former hat factory on the banks of the Chicago River features newly renovated and richly decorated rooms.
Unavailable
Hip
DEAL
21c Museum Hotel Chicago
$179
95%
|
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Downtown
was on HT
$195
This boutique hotel also houses its very own art museum filled with 21st-century pieces from emerging artists.
Unavailable
3 Rooms Left
Solid
DEAL
Level Chicago - Fulton Market
$234
90%
|
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Downtown
was on HT
$279
The outdoor pool takes vacay vibes to new heights.
Unavailable
Solid
ACME Hotel Company Chicago
$129
93%
|
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River North
was on HT
$139
Playful-meets-industrial-chic design with bold, colorful and artistic accents.
Unavailable
Luxe
Sofitel Chicago Magnificent Mile
$309
96%
|
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Gold Coast
was on HT
$319
Walking distance to the Magnificent Mile? Check. Lakefront trail? Check. Public transportation? Check.
Unavailable
2 Rooms Left
Luxe
Loews Chicago Hotel
$399
96%
|
–
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
Solid
DEAL
LEVEL Chicago - Old Town
$468
89%
|
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Downtown
was on HT
$519
Stay fit in the fitness center, or head outside for bocce ball or a game of hoops on the rooftop basketball court.
Unavailable
Luxe
Omni Chicago Hotel
$249
90%
|
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Magnificent Mile
was on HT
$399
Ideal Mag Mile address just steps from endless shopping & world-class eateries.
Unavailable
1 Room Left
Solid
Courtyard by Marriott Chicago at Medical District / UIC
$219
92%
|
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Downtown
was on HT
$229
Spot-on location for all things medical campus – near UIC Chicago and Rush. PS: Little Italy dining nearby too(!).
Unavailable
Basic
Sonesta Simply Suites Chicago Waukegan
$133
82%
|
–
Downtown
Suite-style rooms offer up max 'home away from home' vibes.
Unavailable
2 Rooms Left
Basic
The Champagne Lodge & Luxury Suites
$95
87%
|
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Western Suburbs
was on HT
$127
En suite deets include a whirlpool bath, walk-in shower, fireplace and plenty of serene styling.
Unavailable
Solid
DEAL
Chez Hotel
$117
97%
|
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North Suburbs
was on HT
$176
The newly opened rooftop bar & restaurant is a must when you’re in the mood to wine and dine with a side of stellar views.
Unavailable
Basic
City Suites Hotel
$122
87%
|
–
Lakeview
was on HT
$217
A super recent reno has left rooms lookin’ pret-ty darn fresh. Style’s sleekly Art Deco, with pops of whimsy.
Unavailable
3 Rooms Left
Solid
DEAL
Springhill Suites Chicago O'Hare
$110
92%
|
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ORD
was on HT
$150
Catch a free shuttle ride to/from O’Hare airport or to the CTA train station which’ll zip you into the city in no time. (Museums await!)
Unavailable
1 Room Left
HighRoller
The Emily Hotel - Loft Suite
$349
–
West Loop
Spacious 545 sq ft suite
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