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Chicago stands a strong chance of being everyone's kind of town. With world-class museums and performing arts venues, legendary jazz and blues clubs, more than 7,000 restaurants serving everything from haute cuisine to hot dogs, and 29 magnificent miles of lakefront, the "City of Big Shoulders" offers something for everyone.
For gravity-defying architecture, a world-class music scene fueled by thousands of restaurants, and cosmopolitan comforts without the big-city attitude.
$135+: Low weekend domestic fares (round-trip) Major Providers
$66+: Nationwide summer/fall fare sale (one-way) AirTran
$254*+: Everyday low fares thru November (each way) United
Up to 60% off: US city fares from $105 (round-trip) Major Airlines
$254*+: Low domestic fares to top cities (one-way) United
$102+: Labor Day flight sale to US cities (round-trip) Major Providers
$110+: Reduced summer US airfares (round-trip) Major Airlines
$53/nt+: Avenue Garden Hotel by New Orleans streetcar Orbitz
Up to 30% off: Early-summer hotels with breakfast & more Hotels.com
$139/nt+: Midtown Atlanta landmark, Georgian Terrace Hotel Orbitz
$279/nt+: Chicago Hotel Sax w/breakfast, wine Perfect Escapes
30% off: Summer weekday hotel sale in top cities Hotels.com
$315/nt+: Chicago 4-star w/late check-out, breakfast Sutton Place Hotel
$279/nt+: Chicago Hotel Sax w/VIP passes, breakfast Perfect Escapes
$54/nt+: Red hot hotel bargains in major US cities Hotels.com
$395/nt+: 5-star The Peninsula Chicago Expedia
$283+: Bargain Chicago 2-nt trip w/flight & hotel Major Airlines
$498+: 4-nt spa trips w/upscale beach & city resorts Major Providers
$587+: 3-night Chicago trip with Hilton stay & flight Travelocity
$61+: Last-min domestic trips w/hotel & rental car Major Providers
$451+: 3-star Sheraton Gateway Suites Chicago O'Hare Expedia
$13.95+: July 4th car rentals in Chicago, LA & more Hotwire
Up to $3 off: Service to and from the airport American Express
A diverse array of lodging options abound in Chicago, from the grand and luxurious hotels of Magnificent Mile to nearby boutique properties and budget options geared toward value-conscious travelers.
City Suites Hotel
Set on busy Belmont Avenue, where real locals live, you’ll find plenty of hip eateries and happening nightlife, as well...
Hotel Cass
The Hotel Cass has teamed up with Holiday Inn Express to transform the former no-frills hotel into a beautifully chic boutique...
Ohio House Motel
For location, price and the nostalgia factor, you can’t beat this strictly no-frills, mid-century motor lodge located in...
Hotel Burnham
This century-old National Historic Landmark is home to the extravagant boutique, Hotel Burnham, located in The Loop across...
The James
All heads turned when this luxury boutique hotel opened in 2006. Think modern, white rooms, the swanky J Bar, and David...
Hotel Indigo Chicago
The stylish Hotel Indigo Chicago debuted in May 2005, bringing an innovative and inspirational lodging experience to...
Park Hyatt Chicago
The Hyatt chain is Chicago based, so naturally its flagship property is a real stunner. In addition to its perfect Magnificent...
The Drake
The famous lakefront property is marvelously elegant, with a magnificent setting that never fails to attract a slew of royalty...
The Peninsula
This extravagant hotel’s wow factor is undeniable. The lobby features soaring white-marble walls that lead to a...
City Suites Hotel
Set on busy Belmont Avenue, where real locals live, you’ll find plenty of hip eateries and happening nightlife, as well...
Hotel Cass
The Hotel Cass has teamed up with Holiday Inn Express to transform the former no-frills hotel into a beautifully chic boutique...
Ohio House Motel
For location, price and the nostalgia factor, you can’t beat this strictly no-frills, mid-century motor lodge located in...
City Suites Hotel
Set on busy Belmont Avenue, where real locals live, you’ll find plenty of hip eateries and happening nightlife, as well...
Hotel Burnham
This century-old National Historic Landmark is home to the extravagant boutique, Hotel Burnham, located in The Loop across...
The James
All heads turned when this luxury boutique hotel opened in 2006. Think modern, white rooms, the swanky J Bar, and David...
Hotel Burnham
This century-old National Historic Landmark is home to the extravagant boutique, Hotel Burnham, located in The Loop across...
Hotel Indigo Chicago
The stylish Hotel Indigo Chicago debuted in May 2005, bringing an innovative and inspirational lodging experience to...
Park Hyatt Chicago
The Hyatt chain is Chicago based, so naturally its flagship property is a real stunner. In addition to its perfect Magnificent...
The Drake
The famous lakefront property is marvelously elegant, with a magnificent setting that never fails to attract a slew of royalty...
The James
All heads turned when this luxury boutique hotel opened in 2006. Think modern, white rooms, the swanky J Bar, and David...
The Peninsula
This extravagant hotel’s wow factor is undeniable. The lobby features soaring white-marble walls that lead to a...
Don't forget to pack your appetite. With incredible four-and five-star restaurants, innovative fusion hot spots, the best deep-dish pizzerias in the world (the pie was invented here!), and a McDonald's furnished with chairs by Le Corbusier, Chicago offers an array of dining options, from ultra-high-end to super budget.
Avec
Top chefs and eager locals crowd together at communal tables to nosh on to-die-for Mediterranean small plate dishes like...
Tank Sushi
Gastro-centric Lincoln Square has its finest culinary expression at this much ballyhooed fresh-from-the-sea sushi and Japanese...
Foodlife
Tired shoppers seek refueling at this basement collection of fancy food stands where guests can choose from over a dozen...
The Wiener's Circle
This iconic hot dog stand is where drunken North Siders come to trade barbs with the acerbic staff and dine on greasy food....
Moto
Chef Homaro Cantu’s marriage of food and science has rocked the culinary world. Think servers in lab coats, edible menus,...
Sepia
This West Loop newbie has already been dubbed an instant classic. Think roasted rabbit with ricotta dumplings or slow baked...
Sixteen
“The Donald” is determined to put his indelible stamp on Chicago’s dining scene and he’s set to do so...
The Signature Room and Lounge
At the bar and restaurant on the 95th and 96th floors of the John Hancock building you can have cocktails and a sumptuous...
Avec
Top chefs and eager locals crowd together at communal tables to nosh on to-die-for Mediterranean small plate dishes like...
Tank Sushi
Gastro-centric Lincoln Square has its finest culinary expression at this much ballyhooed fresh-from-the-sea sushi and Japanese...
Foodlife
Tired shoppers seek refueling at this basement collection of fancy food stands where guests can choose from over a dozen...
The Wiener's Circle
This iconic hot dog stand is where drunken North Siders come to trade barbs with the acerbic staff and dine on greasy food....
Moto
Chef Homaro Cantu’s marriage of food and science has rocked the culinary world. Think servers in lab coats, edible menus,...
Sepia
This West Loop newbie has already been dubbed an instant classic. Think roasted rabbit with ricotta dumplings or slow baked...
Sixteen
“The Donald” is determined to put his indelible stamp on Chicago’s dining scene and he’s set to do so...
The Signature Room and Lounge
At the bar and restaurant on the 95th and 96th floors of the John Hancock building you can have cocktails and a sumptuous...