Chicago Vacation Packages

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Top Chicago Flight + Hotel Deals

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Hyatt Regency Chicago
Selina Chicago
Chicago Athletic Association, part of Hyatt
Chicago South Loop Hotel

Where to stay in Chicago

Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago

Top Hotels in Chicago

The Whitehall Hotel
The Whitehall Hotel
4 out of 5
105 E Delaware Pl, Chicago, IL, 60611
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from Jul 6 to Jul 7
3.9/5 Very Good! (3,246 reviews)
"Excellent location. Walking distance to restaurants, plenty of shopping, public transportation and Lake Michigan. Staff is always wonderful and accommodating. The room was very clean and comfy."

Reviewed on Jun. 24, 2022

The Whitehall Hotel
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL, 60605
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Jul 6 to Jul 7
3.7/5 Good! (3,857 reviews)
"The Congress Hotel was everything we needed it to be. It’s location is ideal for anyone that wants to be right in the center of everything downtown has to offer. It has the charm of an old hotel, so if you’re expecting a brand new, shiny hotel experience you might not get what you’re looking for ..."

Reviewed on Jun. 22, 2022

Congress Plaza Hotel
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago
2 out of 5
65 E Harrison St, Chicago, IL, 60605
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from Jul 6 to Jul 7
3.2/5 (1,175 reviews)
"This is an older hotel but the key here is location, location, location.Staff was lovely"

Reviewed on Jun. 21, 2022

Travelodge by Wyndham Downtown Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Chicago Vacation Packages

A modern metropolis on the shores of Lake Michigan that’s defined by a love for fine art, baseball and the blues.

Stroll museums and parks filled with art, and catch live blues any night of the week in Chicago’s bustling Downtown district. Or catch a lively sports game in this home to the Cubs and White Sox baseball teams, and the Chicago Bulls basketball team.

This metropolis is the third largest city in America, but getting around is easy thanks to the efficient above ground train, the ‘L’. Get your bearings from the tallest skyscraper in the US, Willis Tower, which defines the city’s skyline. The viewing platform, 1,353 feet (412 meters) above the busy streets, offers unparalleled vistas of Lake Michigan, Navy Pier, and other main attractions.

Lincoln Park, just north of downtown, has beaches, sporting grounds and landscaped gardens. Soak up the history of the Windy City at the Chicago History Museum, located on the southern end of the park. Take a stroll through the indoor gardens of the Lincoln Park Conservatory, or spend an afternoon at the Lincoln Park Zoo. This public zoo houses more than 1,000 animals. Brookfield Zoo, 12 miles west of the city center, is more than double the size and features dolphin displays, big cats, a variety of primates and more.

Head back into the Loop district downtown for some of the best shopping in the city, along Michigan Avenue’s Magnificent Mile. It’s a good place for lunch or dinner, or people watching while you sip a coffee or beer. Just south of the Magnificent Mile is the expansive Art Institute of Chicago well worth a visit for its collection of European and American masterpieces that include Monet, Van Gogh, and much more. Nearby is Millennium Park, a meeting place with public art and spectacular summer concerts.

Chicago’s Museum Campus is located in the South Loop, just a few miles by car or a few stops on the “L” from downtown. The Field Museum is filled with natural history, while the Museum of Science has interactive exhibits such as a mock coal mine and an airplane.

Some of America’s most influential figures came from Chicago. Visit the Ernest Hemingway Museum and House, where the famous writer was born. Architect Frank Lloyd Wright’s first house is in the pretty Oak Park neighborhood (called the Frank Lloyd Wright Home and Studio). He designed many houses and buildings in the area, including Unity Temple, considered one of his best. On your way back into town, stop off at the Garfield Park Conservatory, an urban oasis of rare and exotic plants.

No trip to Chicago would be complete without catching a baseball game at the legendary Wrigley Field. At night, head to Navy Pier, packed with lively bars and restaurants. Another option is to head out for a night of blues at one of Chicago's legendary clubs. Check out B.L.U.E.S. near downtown on Chicago's north side or Kingston Mines a few miles north near Lincoln Park. Both of these long established venues have music every night of the week.

Frequently asked questions

Your guide to Chicago Vacations

From the Loop and Lake Michigan to baseball and blues, Chicago is a city that simply screams American style.

The Second City

Though Los Angeles is undeniably the country's second-largest spot, Chicago holds a special place in the collective heart of the United States. Since its founding in the early 19th century, this take-no-prisoners town has played host to gangsters and legends, presidents and pioneers, and some of the most iconic jazz and blues spots this side of the Mississippi. It's almost symbolic of the nation's fierce independence; despite the glossy updates to its shopping strips and tourist attractions, Chicago still operates with a bold, brash ethos.

A World-Class Destination

Believe the hype: packages for Chicago IL are every bit as exciting as those in Los Angeles and New York. The landscape may be different — Chicago's skyline tends toward the futuristic, for instance, and its upscale districts are uniquely vibrant — but the cultural attractions are on par with the world's best. This is, above all, a powerhouse of a city, and that no-holds-barred attitude is evident in everything from the art museums to the cutting-edge restaurants.

Beyond the Breeze

Of course, there's a reason they call it the Windy City. Thanks to its position on Lake Michigan, this metropolis is subject to a relatively constant breeze. The seasons here are clearly defined with scorching summers and freezing winters, so you'll generally find the most comfortable temps in the transitional periods. Don't discount those high-season months however: Some of the best packages and cheap deals are available on hotels in Chicago when the mercury moves into the extremes.

Top Things to See and Do

Unless you're staying for several weeks, you'll need a tightly coordinated itinerary to hit the hottest sights. Lincoln Park is the best spot for bustling beaches and gorgeous gardens, and its associated Lincoln Park Zoo is designed to make any animal lover swoon. Wrigley Field is a must for baseball fans, but head straight for Navy Pier when the sun goes down. The city's most effervescent clubs and restaurants are situated in the area, and you can easily head to the North Side for its iconic blues joints. If you rent a car in Chicago, set it aside for your downtown adventures. The L is more than sufficient.

Chicago Deals, Discounts, and More

Before you make a beeline for the city's borders, browse the travel tools at Expedia to find the latest holiday packages combining your accommodations and flight deals to Chicago. Chi-Town getaways have never looked so sweet.

Popular places to visit in Chicago

Top things to do in Chicago