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Chicago Flight + Hotel packages

Cheap Chicago Hotels

See all 936 Hotels in Chicago
Central Loop Hotel

Central Loop Hotel

111 West Adams Street, Chicago
4.5 out of 5.0
4.1 out of 5 (44 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 ...

$76

$76
River Hotel

River Hotel

75 East Wacker Drive, Chicago
4.5 out of 5.0
4.1 out of 5 (30 reviews)

Located in The Loop, this hotel is within a 10-minute walk of Chicago Theatre, Wrigley Building, and Tribune Tower. Ford Center for the Performing Arts Oriental ...

$68

$68
The Whitehall Hotel

The Whitehall Hotel

105 E Delaware Pl, Chicago
4.0 out of 5.0
3.8 out of 5 (133 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.

$67

$67
Wyndham Grand Chicago Riverfront

Wyndham Grand Chicago Riverfront

71 E Wacker Dr, Chicago
4.5 out of 5.0
4.4 out of 5 (16 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 ...

$97

$97
Edward Hotel Chicago

Edward Hotel Chicago

6600 N. Mannheim Rd, Rosemont
3.5 out of 5.0
3.9 out of 5 (20 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
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago
3.0 out of 5.0
4.0 out of 5 (7 reviews)

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

$79

$79
Hotel Felix Chicago

Hotel Felix Chicago

111 W Huron St, Chicago
4.5 out of 5.0
4.0 out of 5 (18 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, ...

$79

$79
Loews Chicago Hotel

Loews Chicago Hotel

455 North Park Drive, Chicago
5.0 out of 5.0
4.0 out of 5 (6 reviews)

Located in Near North Side, this luxury hotel is within a 10-minute walk of Tribune Tower and Wrigley Building. Navy Pier and Chicago Children's Museum are also ...

$139

$139
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

Ohare International Airport, Chicago
4.5 out of 5.0
3.9 out of 5 (15 reviews)

The only hotel on airport property, the Hilton Chicago O'Hare Airport is located 2 miles from the Donald E. Stephens Convention Center and the Rosemont Theatre, ...

$119

$119
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

17 E Monroe St, Chicago
4.0 out of 5.0
4.0 out of 5 (48 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 ...

$109

$109
Map

Your Chicago vacation

From food to theater and Lake Michigan to the Loop, Chicago is home to some equally big names. But you don't need to fly in on Obama's Air Force One or have pockets as deep as Oprah to be able to experience a Chicago vacation at its fullest. Take a stroll down the Magnificent Mile, catch a Cubs game at Wrigley Field, and soak up the waterfront culture of the Second City.

Before you rush to Millennium Park, allow CheapTickets to help you with the planning. We'll share the city's top highlights that will blow your mind -- without blowing your budget.

Best time to take a vacation to Chicago

If you visit Chicago in the early fall you will experience the best of its weather as it retains its warm temperatures but loses the humidity of the summer months. Spring time is cooler, and it is a good time to capture those cheaper flights and hotels. The Chicago Blues Festival every June attracts headline acts from around the country and is extremely popular, as is the early three-day snow sculpturing exhibition held every winter on Navy Pier. Grant Park at the harbor hosts an annual Taste of Chicago Food Festival which, as you might expect, appeals to a wide audience.

Insider tips for Chicago travel

Alta Vista Terrace

Capture the history of Alta Vista Terrace close to Wrigley Field, modeled on a block of row houses in London.

Cafe Selmarie

Take lunch at the charming Cafe Selmarie overlooking the Lincoln Square Fountain and consume some mouth-watering cakes.

Montrose Harbor

Walk the lake-front trail north towards Montrose Harbor with some incredible views of the city skyline.

Ping Tom Memorial Park

Admire the Oriental architecture on a steady stroll through the pleasant and quiet surroundings of Ping Tom Memorial Park.

Pancho Pistolas

Dine out at Pancho Pistolas restaurant serving delicious Mexican cuisine in the Bridgeport neighborhood.

Chicago highlights

Lincoln Park Zoo

For an easy escape without having to spend a cent on your Chicago travels, take the afternoon to meander through the menagerie at the Lincoln Park Zoo. Not only is it brimming with wildlife exhibits and beautiful historical architecture, it's totally free and open 365 days a year.

Magnificent Mile

The Mag Mile is a revered for its incredible shopping and eating scene, as well as the festivities that occur throughout the year. Lined by colorful tulips in the springtime and glittering lights during the holidays, the Mag Mile is chockablock with department stores and notable landmarks, from the Wrigley Building to Oak Street Beach. For incredible views on your Chicago travels, head to the Hancock Observatory or spend a few bucks on a cocktail in the Signature Lounge.

Cultural Chicago

If you want to experience the cultural side of the Second City on your Chicago vacation, make a beeline for the Chicago Cultural Center where admission is free. After taking in the impressive architecture and stunning Tiffany dome, head to the Art Institute across the street to view the amazing collection of Impressionist art and the new Modern Wing. Take a stroll to the Buckingham Fountain and laze in the sun, or take in a nighttime light show.

Navy Pier

For a bustling carnival vibe along Lake Michigan, wander along the Navy Pier promenade and catch the spirit of Chicago. Bring the kids to the Children's Museum, Shakespeare Theatre or Stained Glass Gallery, and marvel at the incredible skyline views from the 150-foot Ferris wheel. Grab a bite to eat at Chicago institution Harry Caray's, and rest your weary feet to enjoy the free weekly fireworks.

Millennium Park

Chicago has plenty of parks, but this one is worth a special mention. An impressive feat of engineering, landscaping and cultural celebration, Millennium Park is home to the iconic Cloud Gate sculpture and splashy Crown Fountain video sculpture. Enjoy a concert at Jay Pritzker Pavilion, the go-to spot for the best in outdoor entertainment.

* 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.