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Local Getaways
Find the best hotels within 350 miles for a spontaneous adventure.
Cincinnati
Cleveland
Indianapolis
Charlottesville
Niagara Falls, ON
Unavailable
Luxe
DAILY DROP
The Ritz-Carlton, Chicago
$382
95%
|
–
Magnificent Mile
was on HT
$545
Can’t-be-beat address on the Magnificent Mile (!).
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Unavailable
Hip
DEAL
The Allegro Royal Sonesta Hotel Chicago Loop
$108
90%
|
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Loop
was on HT
$181
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
2 Rooms Left
Solid
DEAL
Hyatt House Chicago - Medical / University District
$104
95%
|
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West Side
was on HT
$196
Smart, stylish digs in the masssssive, architecturally impressive former Cook County Hospital building. (It’s a stunner!)
Unavailable
Hip
DEAL
Hyatt Centric The Loop Chicago
$120
95%
|
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Loop
was on HT
$149
Loop location means you're steps from the bustling Financial District and (far bustlier) Theater District.
Unavailable
Hip
Ambassador Chicago
$65
92%
|
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Gold Coast
was on HT
$189
Sleek, modern and eclectic design welcomes the beautiful people. Now you can be one of them!
Unavailable
3 Rooms Left
Basic
DEAL
Home2 Suites by Hilton Chicago River North
$123
89%
|
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Downtown
was on HT
$216
Stellar River North location makes urban exploring a breeze.
Unavailable
Basic
DEAL
Hampton Inn Chicago Orland Park
$122
94%
|
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West Side
was on HT
$135
Unavailable
2 Rooms Left
Solid
DEAL
Hilton Garden Inn Chicago McCormick Place
$139
95%
|
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Loop
was on HT
$299
Polished flair throughout, with soaring ceilings and designery touches. Adjacent to the new Wintrust Arena, if that’s where you’re headed.
Unavailable
1 Room Left
Charming
DEAL
Wicker Park Inn
$168
94%
|
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Wicker Park
was on HT
$209
Drops ya in the heart of a vibrant, trendier-than-thou ‘hood teaming with vintage shopping, cool eateries & hoppin’ nightlife.
Unavailable
Luxe
DEAL
The Ritz-Carlton, Chicago
$409
95%
|
–
Magnificent Mile
was on HT
$545
Can’t-be-beat address on the Magnificent Mile (!).
Unavailable
3 Rooms Left
Luxe
Pendry Chicago
$289
96%
|
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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
Hip
The Hoxton, Chicago
$288
95%
|
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West Loop
was on HT
$369
This hip London-based brand transformed 3 meatpacking warehouses into a stylish new hotel inspired by the local architecture and galleries.
Unavailable
Luxe
Viceroy Chicago
$345
97%
|
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Gold Coast
It's shimmery and glittering. Makes sense for the Gold Coast locale.
Unavailable
3 Rooms Left
Solid
The Chicago Hotel Collection - Magnificent Mile
$86
83%
|
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Magnificent Mile
was on HT
$178
Modern design and bohemian-chic flair flow throughout this vibrant atmosphere.
Unavailable
Hip
21c Museum Hotel Chicago
$147
95%
|
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Downtown
was on HT
$219
This boutique hotel also houses its very own art museum filled with 21st-century pieces from emerging artists.
Unavailable
2 Rooms Left
Solid
Level Chicago - Fulton Market
$229
89%
|
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Downtown
was on HT
$259
The outdoor pool takes vacay vibes to new heights.
Unavailable
2 Rooms Left
Basic
Majestic Hotel
$149
84%
|
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Lakeview
was on HT
$179
On a quiet residential street, providing a relaxing respite in the bustling city.
Unavailable
Luxe
The Blackstone, Autograph Collection
$319
92%
|
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Loop
was on HT
$369
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
Solid
LEVEL Chicago - Old Town
$319
89%
|
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Downtown
Stay fit in the fitness center, or head outside for bocce ball or a game of hoops on the rooftop basketball court.
Unavailable
Solid
DEAL
Club Quarters Hotel Wacker at Michigan, Chicago
$129
84%
|
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Loop
was on HT
$159
Magnificent Mile’s within a half-mile (read: minimal toting of your shopping spoils required).
Unavailable
Solid
ACME Hotel Company Chicago
$149
93%
|
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River North
was on HT
$199
Playful-meets-industrial-chic design with bold, colorful and artistic accents.
Unavailable
Solid
DEAL
River Hotel
$129
86%
|
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Loop
was on HT
$198
Excellent authentic Italian resto onsite with fab deep dish pizza (natch).
Unavailable
Hip
Freehand Chicago
$130
83%
|
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River North
was on HT
$144
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
Solid
Hotel Chicago West Loop, Sure Stay Collection By Best Western
$149
–
North Side
Bring your furry friends along for the ride. This place is pet friendly.
Unavailable
Basic
Holiday Inn Hotel & Suites Chicago Downtown
$164
82%
|
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Loop
Hit nearby Lou Mitchell’s for breakfast. It’s a Chicago institution and the starting point of Route 66.
Unavailable
Basic
Sonesta Simply Suites Chicago Waukegan
$131
82%
|
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Downtown
Suite-style rooms offer up max 'home away from home' vibes.
Unavailable
Luxe
Omni Chicago Hotel
$324
90%
|
–
Magnificent Mile
was on HT
$359
Ideal Mag Mile address just steps from endless shopping & world-class eateries.
Unavailable
Solid
DEAL
Chicago Marriott Suites Deerfield
$99
96%
|
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Deerfield
was on HT
$539
Separate tub and shower for nighttime soaks and morning clean. Or the other way 'round.
Unavailable
Basic
DEAL
Hilton Garden Inn Warrenville
$99
92%
|
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Naperville
was on HT
$114
Onsite convenience shop stocks snacks, drinks and the toiletries you forgot.
Unavailable
2 Rooms Left
Solid
DEAL
Sonesta Chicago O'Hare Airport Rosemont
$112
91%
|
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Chicago - ORD
was on HT
$152
Harken all ye perpetually-late-for-flights. This place is a mere 3 miles from O’Hare, with a courtesy shuttle to escort you to/from your terminal.
Unavailable
Solid
DEAL
Chez Hotel
$133
97%
|
–
North Suburbs
was on HT
$168
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.
More amazing deals in:
New York City,
Milwaukee,
Las Vegas - Strip,
San Francisco,
Los Angeles,
Boston,
Miami Beach,
Washington, DC,
Denver,
and tons more!