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Chicago Flight + Hotel packages

Chicago Hotels

See all 924 Hotels in Chicago
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago
3.0 out of 5.0
3.1 out of 5 (64 reviews)

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

$86

$86
Edward Hotel Chicago

Edward Hotel Chicago

6600 N. Mannheim Rd, Rosemont
3.0 out of 5.0
3.9 out of 5 (117 reviews)

Situated near the airport, this hotel is 0.4 mi (0.6 km) from Allstate Arena and within 3 mi (5 km) of Rivers Casino and Donald E. Stephens Convention Center. ...

$89

$89
Hyatt Regency Chicago

Hyatt Regency Chicago

151 East Wacker Dr, Chicago
4.0 out of 5.0
4.1 out of 5 (801 reviews)

This Magnificent Mile hotel is located among Chicago's world-class shopping, restaurants and attractions. The Navy Pier, Millennium Park and Art Institute are ...

$119

$119
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

17 E Monroe St, Chicago
4.0 out of 5.0
4.1 out of 5 (770 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 ...

$119

$119
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

163 East Walton Place, Chicago
4.0 out of 5.0
4.1 out of 5 (252 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 ...

$89

$89
Inn of Chicago

Inn of Chicago

162 E Ohio St, Chicago
3.4 out of 5 (314 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 ...

$66

$66
Warwick Allerton Hotel Chicago

Warwick Allerton Hotel Chicago

701 North Michigan Avenue, Chicago
4.0 out of 5.0
4.0 out of 5 (678 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 ...

$83

$83
Chicago's Essex Inn

Chicago's Essex Inn

800 S Michigan Ave, Chicago
3.5 out of 5.0
3.6 out of 5 (338 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, ...

$89

$89
Wyndham Chicago O'Hare

Wyndham Chicago O'Hare

1450 E Touhy Ave, Des Plaines
3.0 out of 5.0
3.9 out of 5 (129 reviews)

Complimentary shuttle service whisks guests arriving from O'Hare International to Wyndham Chicago O'Hare, a mere 2 miles away; concert-goers and hockey fans ...

$75

$75
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 (600 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 ...

$148

$148
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.