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  • Aug 31, 2025Ray HobsonVery reliableThis was my first time using this site and I was very please with how everything was handled. Right after I booked my flight I got a call from one of the associates letting me know i didn't pick out my seats, and choose my seat for my trip there and back from my destination. I was kept up to date in my flight information and they made sure I got my boarding pass. My trip was very stress free. I will be using them again. Thank you!

  • Aug 28, 2025MariaEsperanza EstiloNicko Went Above and BeyondI had to change the return flight of two out of four passengers in our group. Because only half of the group need to travel differently, it took several calls to Iberia Airlines directly and because of the time difference, Nicko coordinated and helped me over a couple of days. Throughout the experience, he explained what he was doing and why he needs to put me on hold and why he needs to call me back the following day, He was very knowledgeable, professional and empathetic to my predicament. Nicko owned the issues and the process and was very transparent with cost and every details of the transactions. I am very grateful and because of him, I will always trust CheapOAir with my travel needs. -Maria E.E.

  • Aug 13, 2025Godswill YakubuBest Travel app to check.You truly get exceptional value for a lower price, and it feels completely fair. Since I started booking with this app, I’ve come to appreciate why they stand out as the best. It’s been a wonderful experience that makes me feel understood and valued as a customer.

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Book Chicago Vacation Packages

CheapOair is offering enormous deals 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.