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Chicago Flight + Hotel packages

Chicago Hotels

See all 887 Hotels in Chicago
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 (205 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 ...

$164

$164
Warwick Allerton Hotel Chicago

Warwick Allerton Hotel Chicago

701 North Michigan Avenue, Chicago
4.0 out of 5.0
4.0 out of 5 (671 reviews)

Located on Michigan Avenue in the middle of Chicago's Magnificent Mile, this 1920s Italian Renaissance hotel is surrounded by fashionable shops, 1 mile from ...

$158

$158
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago
3.0 out of 5.0
3.2 out of 5 (49 reviews)

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

$143

$143
The Whitehall Hotel

The Whitehall Hotel

105 E Delaware Pl, Chicago
4.0 out of 5.0
3.8 out of 5 (1,164 reviews)

Built in 1927, this Chicago hotel is one block from Michigan Avenue shopping and Rush Street restaurants and nightlife; Lake Michigan is within five blocks.

$169

$169
Hotel Felix Chicago

Hotel Felix Chicago

111 W Huron St, Chicago
4.0 out of 5.0
4.0 out of 5 (184 reviews)

Hotel Felix Chicago is 5 blocks from the Magnificent Mile, one of America’s most dazzling thoroughfares. It’s a 7-minute cab ride to the Navy Pier Ferris Wheel, ...

$134

$134
The Palmer House Hilton

The Palmer House Hilton

17 E Monroe St, Chicago
4.0 out of 5.0
4.1 out of 5 (758 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 ...

$191

$191
Chicago's Essex Inn

Chicago's Essex Inn

800 S Michigan Ave, Chicago
3.5 out of 5.0
3.6 out of 5 (329 reviews)

Across from the greenery and attractions of Grant Park, the Essex Inn is 3 blocks from the Loop business district and Lake Michigan, 4 blocks from the Art Institute, ...

$116

$116
Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel

5300 N River Rd, Rosemont
4.5 out of 5.0
4.3 out of 5 (100 reviews)

This family-friendly Rosemont hotel is located near the airport, within a 10-minute walk of Rosemont Theatre and Donald E. Stephens Convention Center. MB Financial ...

$129

$129
Central Loop Hotel

Central Loop Hotel

111 West Adams Street, Chicago
4.0 out of 5.0
4.0 out of 5 (334 reviews)

Situated in the heart of "the Loop," the contemporary Central Loop Hotel is steps from all of Chicago’s major business and cultural destinations such as Chicago ...

$139

$139
Club Quarters Hotel, Central Loop

Club Quarters Hotel, Central Loop

111 West Adams Street, Chicago
4.0 out of 5.0
4.1 out of 5 (595 reviews)

Club Quarters is a club-like hotel in the center of the Loop, Chicago’s central business district. A short walk to Symphony Center, the Art Institute, Board ...

$130

$130
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.