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Local Getaways
Find the best hotels within 350 miles for a spontaneous adventure.
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Unavailable
2 Rooms Left
Luxe
DAILY DROP
The Ritz-Carlton, Chicago
$459
97%
|
–
Magnificent Mile
was on HT
$1,385
Can’t-be-beat address on the Magnificent Mile (!).
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Unavailable
Solid
DEAL
Chez Hotel
$99
89%
|
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Downtown
was on HT
$135
Unavailable
3 Rooms Left
Hip
DEAL
LondonHouse Chicago
$246
97%
|
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Loop
was on HT
$779
Part classic 1920s architecture, part sleek glass tower. All impressive.
Unavailable
Solid
DEAL
Homewood Suites by Hilton Chicago Downtown
$180
97%
|
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Downtown
was on HT
$199
Apartment-style suites in the heart of River North (no real estate agent required).
Unavailable
Solid
DEAL
The Royal Sonesta Chicago River North
$207
94%
|
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River North
Sophisticated and chic, with just enough quirk to keep things cool.
Unavailable
Basic
DEAL
Hampton Inn Chicago Orland Park
$140
86%
|
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West Side
Unavailable
2 Rooms Left
Hip
DEAL
21c Museum Hotel Chicago
$198
95%
|
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Downtown
was on HT
$236
This boutique hotel also houses its very own art museum filled with 21st-century pieces from emerging artists.
Unavailable
2 Rooms Left
Basic
DEAL
Level Chicago - River North
$270
95%
|
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Downtown
You’ll find chic galleries, buzz-worthy restaurants and vibrant nightlife in this hub for arts and entertainment.
Unavailable
Hip
DEAL
The Hoxton, Chicago
$495
95%
|
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West Loop
was on HT
$649
This hip London-based brand transformed 3 meatpacking warehouses into a stylish new hotel inspired by the local architecture and galleries.
Unavailable
1 Room Left
Solid
DEAL
The Chicago Hotel Collection - Magnificent Mile
$131
85%
|
–
Magnificent Mile
was on HT
$191
Modern design and bohemian-chic flair flow throughout this vibrant atmosphere.
Unavailable
Charming
Hotel Chicago West Loop
$178
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
Hip
DEAL
The Allegro Royal Sonesta Hotel Chicago Loop
$279
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
DEAL
Club Quarters Hotel Wacker at Michigan, Chicago
$194
85%
|
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Loop
Magnificent Mile’s within a half-mile (read: minimal toting of your shopping spoils required).
Unavailable
Luxe
DEAL
The Blackstone, Autograph Collection
$297
89%
|
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Loop
was on HT
$469
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
Sonesta Simply Suites Chicago Waukegan
$91
79%
|
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Downtown
Suite-style rooms offer up max 'home away from home' vibes.
Unavailable
2 Rooms Left
Luxe
Pendry Chicago
$580
96%
|
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Loop
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
1 Room Left
Solid
DEAL
LEVEL Chicago - Old Town
$246
90%
|
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Downtown
was on HT
$408
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 Chicago Magnificent Mile
$179
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North Side
was on HT
$228
Free WiFi, so you can brag about your cool trip in real time.
Unavailable
2 Rooms Left
Luxe
The Ritz-Carlton, Chicago
$655
97%
|
–
Magnificent Mile
was on HT
$1,385
Can’t-be-beat address on the Magnificent Mile (!).
Unavailable
Solid
Hilton Garden Inn Chicago McCormick Place
$239
95%
|
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Loop
was on HT
$249
Polished flair throughout, with soaring ceilings and designery touches. Adjacent to the new Wintrust Arena, if that’s where you’re headed.
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
Basic
DEAL
The Chicago Hotel Collection - River North
$80
68%
|
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Downtown
was on HT
$145
Trendy location among the local Near North-ers with easy access to all our favorite downtown haunts.
Unavailable
Luxe
Viceroy Chicago
$545
97%
|
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Gold Coast
was on HT
$895
It's shimmery and glittering. Makes sense for the Gold Coast locale.
Unavailable
Basic
Holiday Inn Hotel & Suites Chicago Downtown
$224
73%
|
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Loop
was on HT
$352
Hit nearby Lou Mitchell’s for breakfast. It’s a Chicago institution and the starting point of Route 66.
Unavailable
Luxe
Waldorf Astoria Chicago
$741
96%
|
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Downtown
was on HT
$1,443
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
DEAL
Holiday Inn Chicago North Shore
$87
82%
|
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Skokie
was on HT
$144
Vibrant atrium with supersized pool lets you get out of your room without facing the weather.
Unavailable
2 Rooms Left
Basic
DEAL
The Champagne Lodge & Luxury Suites
$99
86%
|
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Western Suburbs
was on HT
$112
En suite deets include a whirlpool bath, walk-in shower, fireplace and plenty of serene styling.
Unavailable
Luxe
Loews Chicago O'Hare Hotel
$229
96%
|
–
ORD
Most airport hotels don't have full-time curators to care for their onsite art gallery and exhibition halls.
Unavailable
1 Room Left
Solid
DEAL
Embassy Suites by Hilton Chicago North Shore Deerfield
$145
95%
|
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Deerfield
was on HT
$161
Two-room suites give you plenty of space to stretch out.
Unavailable
Solid
DEAL
Radisson Hotel Schaumburg
$66
87%
|
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North Suburbs
Free shuttle service to O'Hare International Airport as well as shops, restaurants and attractions within a five-mile radius.
Unavailable
Solid
DEAL
Holiday Inn Hotel & Suites Chicago Northwest Elgin
$99
91%
|
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Elgin
was on HT
$115
Convenient location directly off of I-90, but there’s no need to leave in search of sustenance when Bennigan's is onsite.
More amazing deals in:
New York City,
Milwaukee,
Las Vegas - Strip,
San Francisco,
Los Angeles,
Boston,
Miami Beach,
Washington, DC,
Denver,
and tons more!