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Local Getaways
Find the best hotels within 350 miles for a spontaneous adventure.
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Unavailable
Luxe
DAILY DROP
The Ritz-Carlton, Chicago
$417
98%
|
–
Magnificent Mile
was on HT
$595
Can’t-be-beat address on the Magnificent Mile (!).
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Unavailable
3 Rooms Left
Solid
DEAL
Hyatt House Chicago - Medical / University District
$107
94%
|
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West Side
was on HT
$263
Smart, stylish digs in the masssssive, architecturally impressive former Cook County Hospital building. (It’s a stunner!)
Unavailable
Solid
DEAL
Hyatt Place Chicago – Medical / University District
$104
97%
|
–
West Side
was on HT
$253
Goooood-looookin' new digs in the reno’d historic Cook County Hospital (ER fans? Anyone??). Onsite museum documents the landmark’s story.
Unavailable
Hip
DEAL
The Allegro Royal Sonesta Hotel Chicago Loop
$123
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
Solid
DEAL
The Chicago Hotel Collection - Magnificent Mile
$73
85%
|
–
Magnificent Mile
was on HT
$145
Modern design and bohemian-chic flair flow throughout this vibrant atmosphere.
Unavailable
Solid
DEAL
Chez Hotel
$104
88%
|
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Downtown
was on HT
$135
Unavailable
Solid
DEAL
Homewood Suites by Hilton Chicago Downtown
$121
97%
|
–
Downtown
was on HT
$155
Apartment-style suites in the heart of River North (no real estate agent required).
Unavailable
Charming
Hotel Chicago West Loop
$110
81%
|
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West Loop
was on HT
$153
Fitness room is open 24/7, if all that museum-ing wasn’t enough of a workout for you.
Unavailable
1 Room Left
Basic
DEAL
Level Chicago - River North
$192
95%
|
–
Downtown
You’ll find chic galleries, buzz-worthy restaurants and vibrant nightlife in this hub for arts and entertainment.
Unavailable
Solid
DEAL
Hilton Garden Inn Chicago Downtown/Magnificent Mile
$121
85%
|
–
Loop
was on HT
$151
River North location gives you easy access to Chicago’s must-do’s, from shopping/dining to stadium-ing and museum-ing.
Unavailable
Luxe
DEAL
L7 Chicago by LOTTE
$207
96%
|
–
Loop
The former hat factory on the banks of the Chicago River features newly renovated and richly decorated rooms.
Unavailable
Hip
The Hoxton, Chicago
$324
95%
|
–
West Loop
was on HT
$389
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
$200
90%
|
–
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
Solid
DEAL
The Royal Sonesta Chicago River North
$160
94%
|
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River North
Sophisticated and chic, with just enough quirk to keep things cool.
Unavailable
Luxe
Pendry Chicago
$325
96%
|
–
Loop
was on HT
$375
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
Aloft Chicago Mag Mile
$138
91%
|
–
Downtown
was on HT
$217
Stellar Mag Mile location puts the city's best eateries and endless shopping on your doorstep.
Unavailable
Basic
Hampton Inn Chicago Orland Park
$136
80%
|
–
West Side
Unavailable
Luxe
DEAL
The Ritz-Carlton, Chicago
$447
98%
|
–
Magnificent Mile
was on HT
$595
Can’t-be-beat address on the Magnificent Mile (!).
Unavailable
1 Room Left
Charming
DEAL
Wicker Park Inn
$192
94%
|
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Wicker Park
was on HT
$219
Drops ya in the heart of a vibrant, trendier-than-thou ‘hood teaming with vintage shopping, cool eateries & hoppin’ nightlife.
Unavailable
2 Rooms Left
Hip
DEAL
21c Museum Hotel Chicago
$163
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
Solid
DEAL
Level Chicago - Fulton Market
$252
82%
|
–
Downtown
was on HT
$399
The outdoor pool takes vacay vibes to new heights.
Unavailable
3 Rooms Left
Solid
DEAL
LEVEL Chicago - Old Town
$176
90%
|
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Downtown
was on HT
$380
Stay fit in the fitness center, or head outside for bocce ball or a game of hoops on the rooftop basketball court.
Unavailable
2 Rooms Left
Charming
DEAL
The Buckingham Hotel
$229
90%
|
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Loop
was on HT
$329
Right at the Chicago Stock Exchange in the Financial District. Good thing hard work here gets you serious pampering.
Unavailable
Luxe
Viceroy Chicago
$375
97%
|
–
Gold Coast
was on HT
$399
It's shimmery and glittering. Makes sense for the Gold Coast locale.
Unavailable
1 Room Left
Basic
Majestic Hotel
$153
84%
|
–
Lakeview
was on HT
$194
On a quiet residential street, providing a relaxing respite in the bustling city.
Unavailable
Solid
DEAL
Hilton Garden Inn Chicago McCormick Place
$161
95%
|
–
Loop
Polished flair throughout, with soaring ceilings and designery touches. Adjacent to the new Wintrust Arena, if that’s where you’re headed.
Unavailable
Solid
DEAL
Club Quarters Hotel Wacker at Michigan, Chicago
$145
85%
|
–
Loop
was on HT
$216
Magnificent Mile’s within a half-mile (read: minimal toting of your shopping spoils required).
Unavailable
3 Rooms Left
Basic
DEAL
St. Clair Hotel - Magnificent Mile
$112
81%
|
–
Downtown
was on HT
$206
Modern interiors within a cool old building, ideally situated in the heart of the city, steps from the Magnificent Mile.
Unavailable
Luxe
Loews Chicago Hotel
$299
96%
|
–
Magnificent Mile
Head to the rooftop lounge for killer drinks and views (especially if it’s a Navy Pier fireworks night!).
Unavailable
Solid
DEAL
River Hotel
$145
83%
|
–
Loop
was on HT
$216
Excellent authentic Italian resto onsite with fab deep dish pizza (natch).
Unavailable
Hip
citizenM Chicago Downtown
$194
95%
|
–
Loop
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!