Chicago Flight + Hotel packages

Chicago Hotels

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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 (251 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, ...

$80

$80
Hard Rock Hotel Chicago
Hard Rock Hotel Chicago
230 North Michigan Avenue, Chicago
4.0 out of 5.0
4.0 out of 5 (242 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 ...

$97

$97
The Palmer House Hilton
The Palmer House Hilton
17 E Monroe St, Chicago
4.0 out of 5.0
4.1 out of 5 (744 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 ...

$139

$139
Wyndham Grand Chicago Riverfront
Wyndham Grand Chicago Riverfront
71 E Wacker Dr, Chicago
4.0 out of 5.0
4.2 out of 5 (259 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 ...

$101

$101
Hyatt Regency Chicago
Hyatt Regency Chicago
151 East Wacker Dr, Chicago
4.0 out of 5.0
4.1 out of 5 (774 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 ...

$149

$149
Millennium Knickerbocker
Millennium Knickerbocker
163 East Walton Place, Chicago
4.0 out of 5.0
4.1 out of 5 (240 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 ...

$80

$80
Hotel Felix Chicago
Hotel Felix Chicago
111 W Huron St, Chicago
4.0 out of 5.0
4.0 out of 5 (177 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, ...

$99

$99
Congress Plaza Hotel
Congress Plaza Hotel
520 South Michigan Avenue, Chicago
3.0 out of 5.0
3.3 out of 5 (1,275 reviews)

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

$76

$76
The Whitehall Hotel
The Whitehall Hotel
105 E Delaware Pl, Chicago
4.0 out of 5.0
3.8 out of 5 (1,147 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.

$80

$80
Warwick Allerton Hotel Chicago
Warwick Allerton Hotel Chicago
701 North Michigan Avenue, Chicago
4.0 out of 5.0
4.0 out of 5 (640 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
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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.