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Chicago Flight + Hotel packages

Cheap Chicago Hotels

See all 806 Hotels in Chicago
Congress Plaza Hotel

Congress Plaza Hotel

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

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

$143

$143
Club Quarters Hotel, Central Loop

Club Quarters Hotel, Central Loop

111 West Adams Street, Chicago
4.0 out of 5.0
4.2 out of 5 (58 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
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 ...

$191

$191
The Whitehall Hotel

The Whitehall Hotel

105 E Delaware Pl, Chicago
4.0 out of 5.0
3.8 out of 5 (128 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
Chicago's Essex Inn

Chicago's Essex Inn

800 S Michigan Ave, Chicago
3.5 out of 5.0
3.8 out of 5 (25 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
4.2 out of 5 (11 reviews)

This family-friendly Rosemont hotel is located near the airport, within a 10-minute walk of Rosemont Theatre, Fashion Outlets of Chicago, and Donald E. Stephens ...

$129

$129
Warwick Allerton Hotel Chicago

Warwick Allerton Hotel Chicago

701 North Michigan Avenue, Chicago
4.0 out of 5.0
3.9 out of 5 (99 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 ...

$178

$178
Hotel Felix Chicago

Hotel Felix Chicago

111 W Huron St, Chicago
4.0 out of 5.0
4.3 out of 5 (15 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
Hyatt Regency McCormick Place

Hyatt Regency McCormick Place

2233 S Martin Luther King Dr, Chicago
4.0 out of 5.0
3.5 out of 5 (17 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
Central Loop Hotel

Central Loop Hotel

111 West Adams Street, Chicago
4.0 out of 5.0
4.1 out of 5 (43 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
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

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.

Alta Vista Terrace

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

Pancho Pistolas

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

Ping Tom Memorial Park

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

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.

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.

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.

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.

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.

* 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.