Chicago

Cheap flights from Dallas to Chicago (CHI)

DFW — CHI
Nov 5 — Nov 121
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Dallas to Chicago are usually found in January or February, booked 90 days in advance, depart on a Thursday or Friday and return on a Thursday

Find flight deals from Dallas to Chicago

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Popular in

September

Cheapest in

January

Average price

$251
Provider with most accurate pricing for Dallas-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Dallas-Chicago (CHI) flights.
Highest demand for flights based on searches. 14% potential increase in price ($41 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Average for round-trip flights in October 2026
  • Most accurate provider: When it comes to deals on Dallas-Chicago flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Dallas-Chicago flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from Dallas-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Dallas-Chicago flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Dallas-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Dallas to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Dallas with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Dallas to Chicago

How far ahead should I book a flight from Dallas to Chicago?

The best time to book flights from Dallas to Chicago is 89 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Dallas to Chicago?

Currently, January is the cheapest month in which you can book a flight from Dallas to Chicago (average of $196). Flying from Dallas to Chicago in June is currently the most expensive (average of $344). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from DFW to CHI?

When flying from Dallas to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 23% versus a flight in the afternoon.

What is the cheapest day to fly from Dallas to Chicago?

Travelers seeking maximum savings on their Dallas to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

The best insider tips for Dallas to Chicago flights

Cheapflights partnered with top experts to bring you the best recommendations for your Dallas to Chicago trip
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Frontier and Southwest

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Chris Dong

Chris Dong

Expert on DFW

Chris is a consumer travel reporter covering aviation, trending travel news, hotels, and loyalty programs—all for leading global publications like Travel + Leisure, The Washington Post, AFAR, and more. In addition to writing, Chris is a video host for Travel + Leisure, giving consumers an inside look at the latest in air travel.

Reviews of airlines servicing Chicago

See what other customers who have flown with Southwest,Contour, andUnited Airlines from Dallas to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Food

7.0

Overall

7.9

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Dallas to Chicago Travel Guide

Chicago is a large, diverse city known for spectacular architecture, an eclectic arts scene, and lakeside activities along Lake Michigan. A highlight of any trip to this city is Navy Pier, where you can spend time enjoying the shops, restaurants, gardens, parks, and theaters lined along the lake. Art lovers will want to stop by the Art Institute of Chicago or take an architectural boa tour down the Chicago River. There is plenty of evening entertainment to choose from, including the Second City comedy club, Lyric Opera of Chicago, and Shakespeare Theater. Best of all, you can have access to all Chicago has to offer in less than two hours when you choose a direct flight from Dallas.

Both Dallas and Chicago are large cities with much to see and do, so travelers used to city life will feel at home in Chicago. The city is more compact than Dallas, with a larger population, so it may feel more crowded. Sports is a large draw in both cities. Dallas Cowboys fans may be able to catch their team playing the Chicago Bears, while fans of the Mavericks can head to United Center Arena to see them play the Bulls. Chicago's climate is different than Dallas, with cold, snowy winters. If traveling during the winter months, be sure to invest in a good pair of boots, warm coat, gloves, scarves, and a hat. Summers can be hot and humid, so pack lightweight clothing if traveling in this season.

Be sure to use our Cheapflights smart search engine to find the best flight deals, and get ready for your next trip from Dallas to Chicago.

Related info for your journey

  • How long is the flight from Dallas to Chicago?

    Direct flights between Dallas and Chicago are a little under two hours long. Choosing an indirect flight that stops in a connecting city will increase the total travel time.

  • Which airlines operate flights from Dallas to Chicago?

    Several major airlines operate direct flights between Dallas Fort Worth International Airport and Chicago's O'Hare International Airport, including American, United, and Spirit Airlines. Southwest offers flights between Dallas Love field and Chicago Midway International Airport.

  • How frequent are flights between Dallas and Chicago?

    There are close to 200 nonstop flights each week from Dallas to Chicago. There are also many indirect flights, with stopovers in connecting cities such as Atlanta, GA.

  • Which airports serve Dallas to Chicago?

    Dallas is served by two major airports: Dallas Fort Worth International Airport and Dallas Love Field. Chicago is also served by two main airports: O'Hare International Airport and Chicago Midway International Airport.

  • Which direct flight route between Dallas and Chicago is cheapest?

    The cheapest direct flights between Dallas and Chicago are on Spirit and American Airlines, flying from Dallas Fort Worth International Airport to O'Hare International Airport. Those who live closer to Dallas Love Field may find cheaper flights between that airport and Midway International Airport on Southwest.

  • What are the cheapest airlines flying from Dallas to Chicago round-trip?

    According to our current data, Frontier ($66), Southwest ($147), and Contour ($147) offers the cheapest pricing from Dallas to Chicago. Frontier is priced at 73% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Dallas to Chicago one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $40. Southwest flights start at $78 while deals on Contour start at $83 one-way.

  • What are the most popular routes from Dallas to Chicago?

  • What are the most reliable airlines from Dallas to Chicago?

    Before booking your flight to Chicago from Dallas, check out the most reliable airlines to get you to your destination on time: GOL (87%), ITA Airways (83%), Turkish Airlines( 82%).

  • What are the cheapest flights from Dallas to Chicago?

    Looking for the cheapest flight from Dallas to Chicago? While on average our users pay $908, our data indicates the cheapest price to be $129. The most popular route (Dallas/Fort Worth - Chicago O'Hare Intl), is priced around $144.

  • Can I find deals for flights from Dallas to Chicago that include hotel bookings?

    Yes. In addition to deals on Dallas to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Dallas to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Dallas to Chicago.

  • Can I find deals for business class flights from Dallas to Chicago?

    Yes. Cheapflights offers flight deals from Dallas to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Dallas to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Dallas to Chicago (average of $196). Flying from Dallas to Chicago in June is currently the most expensive (average of $344). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

  • What are the most eco-friendly airlines from Dallas to Chicago?

    Southwest Airlines, Spirit Airlines, American Airlines, and United Airlines are among the most eco-friendly airlines with flights to Chicago from Dallas. In addition to providing sustainable nonstop flights, these airlines have taken several steps to foster sustainable travel. United Airlines has heavily invested in sustainable jet fuel and is now introducing fuel-efficient engines with reduced emissions. They also have a carbon offset program offering their passengers the opportunity to compensate for the carbon they produce on each flight. Spirit Airlines has started an onboard recycling program, and they are slowly replacing their fuel-driven ground equipment with more sustainable electric models. American Airlines is also slowly introducing more fuel-efficient aircraft to their fleet and either retiring older models or upgrading them to become more efficient.

  • How can I fly more sustainably from Dallas to Chicago?

    To fly more sustainably, follow these steps: first, carry only what you deem necessary. Avoid overpacking and carrying unnecessary luggage, as this tends to overload the plane. Heavier planes use more fuel to fly, meaning more carbon is introduced into the atmosphere. Second, since you have the option to fly directly to Chicago from Dallas, book a nonstop flight. Avoid booking the cheaper connecting flights since they take off and land twice, introducing much more carbon into the atmosphere. Third, book a flight with an airline that offers a carbon offset program to play your part in reducing the amount of carbon in the atmosphere. Finally, bring your own reusable bottle and headphones on the flight and avoid single-use plastics and disposable headsets.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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Alternative routes for Dallas to Chicago

Top 7 airlines flying from Dallas to Chicago

AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$66Average$221FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$147Average$349FlexibilityNo cancel feeOn-time63%
ContourCheapest$147Average$256FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$166Average$230FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$188Average$361FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$195Average$247FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$210Average$424FlexibilityNo cancel feeOn-time69%

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