Chicago Airfare Deals

The cost of Chicago two-way air tickets is based on historical data, non-warranted and subject to change. Hence, the cost of plane tickets to Chicago and the return journey might vary at the time of booking. The airfares contain base fare, fuel surcharges, our service, and taxes as imposed by the airlines or the airports in question.

* Last updated: Thursday 29th of September 2022 08:54:37 AM

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Types of Chicago Flight Bookings Available

Cheapflightsfreak allows you to discover Chicago flight deals with the world’s best airlines. Compare Chicago airline tickets from the options available, and book one-way or two-way flights to Chicago, direct or nonstop flights to Chicago, last-minute flights to Chicago, red-eye flights to Chicago, one-stop, or two-stop flight to Chicago.

Also, at Cheapflightsfreak, special flight deals are offered on festivals or events like Thanksgiving, Boxing Day, Christmas, New Year, and much more. Booking low-cost flights to Chicago is now easier and faster with responsive and easy-to-use ticket booking engine linked to our website.

Chicago Airports

Chicago is served by four airports, namely, O’Hare International Airport, the world’s second-busiest airport measured by airline operations, Midway International Airport on the Southwest Side, Gary/Chicago International Airport and Chicago Rockford International Airport, located in Gary, Indiana and Rockford. Hence, you have more choices at your fingertips when it comes to booking a cheap flight to Chicago.

How Chicago is connected with the top Domestic Destinations

Rank City Carriers
1 Los Angeles, California American Airlines
2 Denver, Colorado Frontier, Southwest, Spirit, United
3 Seattle/Tacoma, Washington Alaska, Delta, Southwest, Spirit
4 Atlanta, Georgia Delta, Frontier, Southwest, Spirit
5 Chicago–O’Hare, Illinois American, Frontier, Spirit, United

How Chicago is Connected with the Top International Destinations

Rank City Carriers
1 Vancouver, Toronto Air Canada
2 Montreal, Calgary American Eagle
3 London – Heathrow, London -Gatwick (seasonal) British Airways
4 London -Gatwick, Manchester (seasonal) Virgin Atlantic
5 Mexico City Aeroméxico

Best Time to Visit Chicago

The best times to visit Chicago are April through May and between September and October. The temperature remains moderate, warm and the crowd is thin. Moreover, the season allows you to be part of some of the incredible Chicago Comic & Entertainment Expo (April), Chicago Improv Festival (May) and Mayfest (May).

Top Things to Do In Chicago for Families

Chicago has plenty of hotspots for family vacations. A few we have listed here based on the feedback of travelers who booked Chicago flights with us:

  • Willis Tower

    The 110-story skyscraper stands majestically as an identity of Chicago and contributes handsomely to its tourism industry. Recognized as one of the top attractions in the United States it’s visited by more than one million people. It retained the title of world’s tallest building for 25 years since its completion in 1973.

  • Millennium Park

    Looking for the best place for your kids to have fun? Situated in the Loop community area of Chicago in Illinois, this public park has the answer. The area was previously occupied by parkland, Illinois Central rail yards, and parking lots. If you happen to spend your vacation there at the time of Christmas, don’t miss to see the Christmas tree lighting.

  • Cloud Gate

    This public sculpture measuring 33 by 66 by 42 feet (10 by 20 by 13 m) takes visitors by surprise. The architecture and the intelligent mix of shades make it a perfect background for your best selfie. Wondering what makes it so attractive? Well, the credit goes to perfection achieved in their metallurgy? The architecture is built up of 168 stainless steel plates welded together. Want to dig more of the sculpture? Book a cheap air ticket to Chicago now.

  • Navy Pier

    Stop by this 3,300-foot-long (1,010 m) pier on the Chicago shoreline of Lake Michigan to usher in an abode of relaxation, fun, and shopping. The most attractive thing about the place is its Navy Pier Centennial Wheel. The wheel is 200 feet tall – 50 feet taller than the ferris wheel it replaced. There are 42 temperature-controlled gondolas that are accessible around the clock. LEDs circling the wheel’s spokes and rim make it more attractive in the night. Also, the area sees top brands putting their best fashion and lifestyle merchandises on display in its flamboyant stores. The area is home to more than fifty acres of parks, gardens, shops, restaurants, family attractions and exhibition facilities. The place always remains abuzz with activities and crowd. As per a record, it’s visited by more than nine million visitors annually.

Top Things to Do In Chicago for Couples

  • Chicago Helicopter Experience

    Take your romance to a new height with Chicago Helicopter Experience. The company offers many flight services in the day and night hours to let you have an aerial view of Chicago. This is an hour-long flight that makes you witness the Lake Michigan shoreline and many of the city’s iconic sites. Don’t know how to recognize them? No worries. The pilot and the crew are there to share interesting facts about the city and the monuments. The ride is most romantic on a clear night when the Chicago skyline sparkles with light. Wondering about prices? It starts from $148 per person.

  • Green Mill Cocktail Lounge

    This is a music and entertainment paradise. Once a famous hangout for celebrities to the stature of Al Capone, Charlie Chaplin, and Gloria Swanson, the lounge stays open till 4 a.m. each day, and on Saturdays, it stretches further by an hour. So, if you anticipated Chicago vacation as a break for the monotonous schedule, this place is worth getting a vacation. Expect to pay a cover charge from $4-$15, depending on the band.

  • Second City

    Let your love finds an expression. Spend some quality time at the world’s premier comedy troupe, The Second City. The comedy club has served as the launch pad for leading names in the business, including John Belushi, Dan Aykroyd, Mike Myers, Steve Carell, Stephen Colbert, Tina Fey and about 500 others. The close seating and small audience provide an intimate vibe. So, book your cheap flight to Chicago now to have a romantic vacation together.

    Call us today to know more about cheap flight tickets to Chicago. We’re not just limited to booking your flight tickets, but also make sure you get maximum out of your vacation or travel investment.