Beginning of main content

Chicago Vacations

Search Flights

Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Chicago Hotels

Search Flight + Hotel

Advanced options

Chicago Flight + Hotel packages

Chicago Hotels

See all 801 Hotels in Chicago
The Palmer House Hilton

The Palmer House Hilton

17 E Monroe St, Chicago
4.0 out of 5.0
4.1 out of 5 (745 reviews)

This 1925 Beaux Arts-style Chicago hotel is steps from Millennium Park, 2 blocks from Macy's and the Art Institute, and 1 mile from Lake Michigan, Magnificent ...

$159

$159
Chicago South Loop Hotel

Chicago South Loop Hotel

11 W 26th Street, Chicago
3.0 out of 5.0
3.9 out of 5 (36 reviews)

Located in Near South Side, this spa hotel is within 1 mi (2 km) of Illinois Institute of Technology and McCormick Place. US Cellular Field and Soldier Field ...

$93

$93
Kimpton Hotel Allegro

Kimpton Hotel Allegro

171 W Randolph St, Chicago
4.0 out of 5.0
4.1 out of 5 (336 reviews)

Located in the Loop's theater and business districts, Kimpton Hotel Allegro is next to the Cadillac Palace Theatre, 4 blocks from Millennium Park, and 1 mile ...

$179

$179
Hard Rock Hotel Chicago

Hard Rock Hotel Chicago

230 North Michigan Avenue, Chicago
4.0 out of 5.0
4.0 out of 5 (255 reviews)

On Michigan Avenue and across from Millennium Park, this rock-inspired hotel occupies the 36-story, Art Deco-style Carbide and Carbon Building in downtown's ...

$135

$135
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

300 E Ohio St, Chicago
3.5 out of 5.0
3.9 out of 5 (255 reviews)

Located in the northern part of downtown, Doubletree Chicago Magnificent Mile is 2 blocks from Magnificent Mile shopping and dining, 3 blocks from Lake Michigan, ...

$119

$119
Wyndham Grand Chicago Riverfront

Wyndham Grand Chicago Riverfront

71 E Wacker Dr, Chicago
4.0 out of 5.0
4.2 out of 5 (262 reviews)

This 39-story Chicago hotel is across the river from Magnificent Mile shopping, six blocks from Lake Michigan, and a half-mile from the Loop's theater district ...

$144

$144
Millennium Knickerbocker

Millennium Knickerbocker

163 East Walton Place, Chicago
4.0 out of 5.0
4.1 out of 5 (242 reviews)

This 1927 landmark Chicago hotel is a half block from Michigan Avenue/Magnificent Mile shopping, two blocks from Oak Street shopping and Water Tower Place. Lake ...

$118

$118
Hyatt Regency McCormick Place

Hyatt Regency McCormick Place

2233 S Martin Luther King Dr, Chicago
4.0 out of 5.0
4.1 out of 5 (199 reviews)

Connected via enclosed skybridge to the McCormick Place convention complex, the Hyatt Regency is adjacent to a Metro station, with easy access to Chicago's downtown ...

$114

$114
Inn of Chicago, an Ascend Hotel Collection Member

Inn of Chicago, an Ascend Hotel Collection Member

162 E Ohio St, Chicago
3.0 out of 5.0
3.4 out of 5 (299 reviews)

Inn of Chicago is a half-block from the Magnificent Mile and 2 blocks from the landmark Tribune Tower. Millennium Park, Navy Pier, and the Art Institute of Chicago ...

$79

$79
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago
3.0 out of 5.0
3.1 out of 5 (25 reviews)

Built in 1893, this downtown Chicago hotel offers a convenient location across from Grant Park and close to Lake Michigan.

$112

$112
Map

Experience the best of Chicago

With a global smorgasbord of restaurants, bars, music venues and architectural landmarks, Chicago is by no means a Second City. A Chicago vacation brings year-round thrills, whether you're catching the opening pitch at Wrigley Field or riding the famous El.

Before you admire your reflection in Cloud Gate (aka "The Bean") or hit a skyline cruise on Lake Michigan, allow Orbitz to help you with the planning. Enjoy the intel from our insider guide, from the top 10 attractions to tips from local experts.

Best time to take a vacation to Chicago

Tourists flock to Chicago during spring and summer, when Chicagoans emerge from hibernation into outdoor cafes, legendary sports stadiums and the city's gorgeous parks for music, food and cultural festivals including the Taste of Chicago and Lollapalooza.

If a Chicago vacation happens during the winter, pack a down coat and take advantage of off-peak rates at downtown Chicago hotels. The city's public transportation is among the best in the nation, making it easy to travel to museums, bars, restaurants, landmarks and even far-flung locations in the suburbs.

Insider tips for Chicago travel

Boat tours

For a leisurely lesson on Chicago's architecture, catch a boat cruise from Navy Pier or at the bottom of the Wrigley Building.

Alinea

If you're planning to visit this famous restaurant, book your reservation at least two months in advance. If you do score a table, don't be discouraged if you can't spot the restaurant immediately. It's in a grey brick storefront with no sign.

Cocktails

Looking for an offbeat place for cocktails in one of Chicago's hippest neighborhoods? Consider the Bedford in Wicker Park, located in a former bank building. Imbibe old-school cocktails in the actual vault, which is dotted by safe deposit boxes.

Kit Kat Lounge

Shake up your Sunday brunch with the bottomless mimosas and drag shows at Kit Kat Lounge, Boys Town's favorite martini bar and lounge.

Beaches

For great people watching and impressive skyline views, hit Oak Street Beach, where singles flock to play volleyball and sunbathe. Families stick to Montrose and Loyola beaches a little further north, which are a lot less crowded and pose better chances for finding a parking spot.

* Prices reflect the lowest "base rate" found over the next 30 days. Rates are subject to change and may not include taxes and fees, hotel service charges, extra person charges, or incidentals, such as room service. All rates are displayed in USD unless otherwise noted. Converted rates are provided for your convenience. They are based on today's exchange rate, but the hotel will charge you in the local currency.