Canada

Chicago Flight + Hotel Packages

* All rates above were last found on:. These are based on average nightly rates and airfare includes all fuel surcharges, taxes & fees, and our service fees. Hotels, rental cars and activities may have additional taxes and fees. Displayed rates are based on historical data, are subject to change, and cannot be guaranteed at the time of booking. See all booking terms and conditions.

Call for deals too good to be published.
Download Our App

Get CheapOair deals on the GO!

Download
Apply for Our Credit Card

Earn rewards fast. Go where you want!

Learn More
Check Your Flight Status

Get there on time, every time!

Check Status

Book a Vacation Package in Chicago,

CheapOair is offering enormous discounts on Chicago vacation packages. Book Chicago vacations with CheapOair and have a hassle-free vacation. Browse through our list of various packages, and pick the one that suits your budget most. To know more, get in touch our travel experts. Book cheap vacation packages with CheapOair and spend your vacations in Chicago without creating a hole in your wallet!

The global architectural capital, Chicago is a beautiful lakeside city along Lake Michigan in Illinois, US. It is a gleaming bubble wrap of several cultural attractions, sightseeing options, sporting events and superb shopping experiences. This city also wows its visitors with its remarkable outdoor public art and ranks among top 3 prolific movie industry cities after Los Angeles and New York. Chicago’s skyline is dominated by top-class museums, two thousand churches, superstructures and its largest posh shopping destination - the Magnificent Mile.

Things to Do in Chicago

There are plenty of things to do in Chicago. Plan your vacation in the city and book flight tickets with CheapOair for a hassle-free trip.

Art Institute of Chicago

Established in 1879, the Art Institute of Chicago is one of the oldest and largest art museums in the US. It is home to thousands of artworks dating back to several centuries. The museum also contains a top-grade collection of impressionist and post-Impressionist paintings, numerous historical artifacts and specimens of modern and classical art.

Millennium Park

Millennium Park is the top tourist attraction in Chicago and ranks among top 10 in the United States. Some of its highlights are the Jay Pritzker Pavilion (an outdoor concert venue), the interactive Crown Fountain, and the Cloud Gate sculpture on the AT&T Plaza.

Magnificent Mile

The Magnificent Mile is a posh section of Chicago's Michigan Avenue and currently the largest shopping district in Chicago. Its landscape is dotted with a large number of retail, restaurants, museums and hotels that cater to mid and high-end shopping experiences. The Magnificent Mile is famous as the site where the tradition of lighting the trees to start the Christmas season was started more than forty years ago.

Weekend Getaways from Chicago

Milwaukee

Milwaukee is a popular US city located at a couple of hours ride away from Chicago. It is famous as the home of legendary Harley-Davidson motorbikes and is synonymous with German beers since mid-19th century. The city is Guinness Record holder for the world’s largest music festival (Summerfest), and is also known for its Harley-Davidson Museum and Milwaukee Art Museum.

Holland

Located about 150 miles away from Chicago, the city of Holland in Michigan is known for its Dutch heritage and May-bound Tulip Time Festival. During this festival, the city is dotted with millions of tulips in the spring season and visitors are treated to a stunning show of traditional Dutch cuisines, parades, music, and dances. Another famous festival worth checking out here is the Dutch Winterfest that takes place in November.

CheapOair Customer Reviews

  • A most vacation...

    My husband and I loved everything about Las Vegas... The Strips and Fairmount area was amazing. There were so many different attractions to see. You really don't need a rental car, but you must have comfortable shoes to walk up and down the strips. - Petrina  Sep 14, 2021

  • Amazing Nature

    Iceland was amazing. There is so much natural beauty everywhere you look. Lots to see and do if you like the outdoors. What a great trip! - Lynn  Sep 13, 2021

Submit a Review