Compare Cheap Flights from Dallas to Chicago
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Round Trip Flights from Dallas to Chicago
Last updated on Wednesday 04/29/2026 at 05:00 AM, the fares mentioned above are for flight tickets and inclusive of fuel surcharges, service fee and taxes. Based on historical data, these fares are subject to change without prior notice and cannot be guaranteed at the time of booking. Kindly go through our terms and conditions before booking.
Book Dallas To Chicago Flights
Located on the shores of Lake Michigan, Chicago is one of the largest cities in the USA. While most of us recognize the city for its irresistible food, like Chicago deep-dish pizza or Chicago barbecue, there is more to discover. Skyscrapers are the highlight of Chicago. The Willis Tower, 875 North Michigan Avenue, and the Tribune Tower are popular buildings that add more charm to the skyline.
As you plan your Chicago vacation from Dallas, you can add a few tourist spots to your itinerary. The must-visit attractions in the city include the Art Institute of Chicago, Millennium Park, Navy Pier, Cloud Gate, and Lincoln Park Zoo. Furthermore, there are several other activities that you can enjoy, like going on a cruise along the Chicago River or shopping at a local marketplace, and then having time to enjoy beach life and explore gardens.
In addition, if one goes to Chicago between June and August, it is possible to attend different music festivals, such as Lollapalooza and the Chicago Jazz Festival, just to mention a few. Nevertheless, flights from Dallas to Chicago city tend to be full during this period since many people are usually heading there for vacation. Choose shoulder season, April to May and September to October, to book cheap flights from Dallas to Chicago.
Most airlines on this route operate from Dallas-Fort Worth International Airport to O'Hare International Airport. Dallas Love Field and Chicago Midway International Airport also serve as alternate departure and arrival points. Southwest, Spirit, Delta, United, Frontier, and American Airlines operate daily DFW to CHI flights. To know more about cheap flights to Chicago use of search engine to find the cheapest flights from Dallas to Chicago.
Finding Cheap Flights From Dallas To Chicago : Frequently Asked Questions
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How much are round-trip flights from Dallas to Chicago?
Average cost of a round-trip flight from Dallas to Chicago is around $243.
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Which upcoming date is cheapest to fly from Dallas to Chicago?
In the next 90 days, flights from Dallas to Chicago on will be the cheapest on May 15, 2026, May 29, 2026, and May 31, 2026.
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What?s the cheapest day of the week to fly from Dallas to Chicago?
On an average, flights from Dallas to Chicago tend to be cheapest on Friday.
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Which airlines offers the cheapest fares from Dallas to Chicago?
At the moment, SOUTHWEST AIRLINES and ALASKA AIRLINES offer the cheapest flights from Dallas to Chicago.
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When is the peak season for traveling from Dallas to Chicago?
May to July is the peak season to travel from Dallas to Chicago.
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When does the first flight depart from Dallas to Chicago?
The first flight from Dallas to Chicago departs at 09:35 AM.
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When does the last flight from Dallas to Chicago depart?
The last flight from Dallas to Chicago departs at 09:45 PM.
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Cheapest Months to fly to Chicago
The cheapest months to visit Chicago are from May through July.
* The mentioned flight facts are based on the last 3 months' data. Information regarding the highest and lowest booking months is based on the last 12 months' data.
Major Carriers Operating Flights From Dallas To Chicago
SOUTHWEST AIRLINES
$116
$219
ALASKA AIRLINES
$264
$321
Low Cost Carriers Operating Flights From Dallas To Chicago
SOUTHWEST AIRLINES
$116
$219
ALASKA AIRLINES
$264
$321
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