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Everything you should know
Flight Deals
Cheap Flights from Dallas to Chicago
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Dallas to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.
Recent round-trip flight deals from Dallas to Chicago
Sat, Feb 6 - Tue, Feb 16
4:50 pm - 11:46 pmDFW Dallas/Fort Worth-MDW Chicago Midway
6h 56m1 stop Atlanta Hartsfield-Jackson
1:18 pm - 7:30 pmMDW Chicago Midway-DFW Dallas/Fort Worth
6h 12m1 stop Atlanta Hartsfield-Jackson
$169Frontier
Fri, Feb 5 - Wed, Feb 17
4:50 pm - 11:46 pmDFW Dallas/Fort Worth-MDW Chicago Midway
6h 56m1 stop Atlanta Hartsfield-Jackson
6:01 am - 8:46 amMDW Chicago Midway-DFW Dallas/Fort Worth
2h 45mnonstop
$170Frontier
Tue, Dec 1 - Tue, Dec 8
9:30 am - 2:15 pmDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
4h 45m1 stop Kirksville Cannon Memorial
10:00 am - 12:50 pmORD Chicago O'Hare Intl-DFW Dallas/Fort Worth
2h 50mnonstop
$189Multiple Airlines
Thu, Nov 19 - Tue, Dec 1
9:30 am - 2:15 pmDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
4h 45m1 stop Kirksville Cannon Memorial
9:13 am - 12:09 pmORD Chicago O'Hare Intl-DFW Dallas/Fort Worth
2h 56mnonstop
$192Multiple Airlines
Sat, Dec 5 - Sat, Dec 5
9:51 am - 12:24 pmDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
2h 33mnonstop
3:04 pm - 5:50 pmORD Chicago O'Hare Intl-DFW Dallas/Fort Worth
2h 46mnonstop
$194American Airlines
Sat, Dec 12 - Sat, Dec 12
5:25 pm - 7:59 pmDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
2h 34mnonstop
9:06 pm - 11:42 pmORD Chicago O'Hare Intl-DFW Dallas/Fort Worth
2h 36mnonstop
$194American Airlines
Wed, Dec 9 - Sat, Dec 12
8:25 pm - 10:40 pmDAL Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
6:00 am - 8:35 amMDW Chicago Midway-DAL Dallas Love Field
2h 35mnonstop
$199Southwest
Wed, Dec 2 - Wed, Dec 9
8:25 pm - 10:40 pmDAL Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
8:50 am - 11:20 amMDW Chicago Midway-DAL Dallas Love Field
2h 30mnonstop
$199Southwest
Tue, Dec 1 - Tue, Dec 8
12:39 pm - 3:06 pmDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
2h 27mnonstop
12:17 pm - 3:08 pmORD Chicago O'Hare Intl-DFW Dallas/Fort Worth
2h 51mnonstop
$199United Airlines
Tue, Dec 8 - Wed, Dec 16
7:53 pm - 10:26 pmDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
2h 33mnonstop
5:52 pm - 11:30 pmORD Chicago O'Hare Intl-DFW Dallas/Fort Worth
5h 38m1 stop Houston George Bush Intcntl
$209United Airlines
Recent one-way flight deals from Dallas to Chicago
Mon, Jan 18
8:35 pm - 11:46 pmDFW Dallas/Fort Worth-MDW Chicago Midway
27h 11m1 stop Atlanta Hartsfield-Jackson
$106Frontier
Sun, Jan 17
5:01 am - 11:46 pmDFW Dallas/Fort Worth-MDW Chicago Midway
18h 45m1 stop Atlanta Hartsfield-Jackson
$108Frontier
Tue, Dec 1
11:45 am - 4:15 pmDAL Dallas Love Field-MDW Chicago Midway
4h 30m1 stop Nashville Intl
$110Southwest
Tue, Dec 1
6:50 pm - 10:45 pmDAL Dallas Love Field-MDW Chicago Midway
3h 55m1 stop Nashville Intl
$110Southwest
Sat, Dec 5
7:15 am - 3:04 pmDFW Dallas/Fort Worth-MDW Chicago Midway
7h 49m1 stop Atlanta Hartsfield-Jackson
$110Delta
Wed, Dec 2
6:12 am - 12:04 pmDAL Dallas Love Field-MDW Chicago Midway
5h 52m1 stop Atlanta Hartsfield-Jackson
$110Delta
Wed, Jan 27
10:45 am - 1:15 pmDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
2h 30mnonstop
$113United Airlines
Mon, Nov 23
9:30 am - 2:15 pmDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
4h 45m1 stop Kirksville Cannon Memorial
$117Contour
Tue, Nov 10
9:30 am - 2:15 pmDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
4h 45m1 stop Kirksville Cannon Memorial
$117Contour
Sat, Nov 21
8:43 pm - 11:15 pmDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
2h 32mnonstop
$121United Airlines
Recent last minute flight deals from Dallas to Chicago
Sat, Nov 7 - Wed, Dec 9
8:54 am - 11:25 amDFW Dallas/Fort Worth-MDW Chicago Midway
2h 31mnonstop
10:40 am - 1:14 pmMDW Chicago Midway-DFW Dallas/Fort Worth
2h 34mnonstop
$187Frontier
Mon, Nov 9 - Mon, Nov 9
6:50 am - 9:22 amDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
2h 32mnonstop
8:30 pm - 11:27 pmORD Chicago O'Hare Intl-DFW Dallas/Fort Worth
2h 57mnonstop
$189Frontier
Mon, Nov 9 - Thu, Nov 19
9:30 am - 2:15 pmDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
4h 45m1 stop Kirksville Cannon Memorial
8:30 pm - 11:27 pmORD Chicago O'Hare Intl-DFW Dallas/Fort Worth
2h 57mnonstop
$215Multiple Airlines
Mon, Nov 9 - Thu, Nov 19
9:30 am - 2:15 pmDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
4h 45m1 stop Kirksville Cannon Memorial
8:30 pm - 11:27 pmORD Chicago O'Hare Intl-DFW Dallas/Fort Worth
2h 57mnonstop
$216Multiple Airlines
Mon, Nov 9 - Thu, Nov 12
9:30 am - 2:15 pmDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
4h 45m1 stop Kirksville Cannon Memorial
2:55 pm - 7:15 pmORD Chicago O'Hare Intl-DFW Dallas/Fort Worth
4h 20m1 stop Kirksville Cannon Memorial
$261Contour
Mon, Nov 9 - Wed, Nov 11
9:30 am - 2:15 pmDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
4h 45m1 stop Kirksville Cannon Memorial
2:55 pm - 7:15 pmORD Chicago O'Hare Intl-DFW Dallas/Fort Worth
4h 20m1 stop Kirksville Cannon Memorial
$263Contour
Fri, Nov 6 - Tue, Dec 8
10:55 pm - 1:10 amDAL Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
7:05 am - 9:35 amMDW Chicago Midway-DAL Dallas Love Field
2h 30mnonstop
$324Southwest
Fri, Nov 6 - Sat, Dec 5
10:55 pm - 1:10 amDAL Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
6:00 am - 8:35 amMDW Chicago Midway-DAL Dallas Love Field
2h 35mnonstop
$324Southwest
Mon, Nov 9 - Sat, Nov 21
1:52 pm - 6:30 pmDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
4h 38m1 stop Detroit Metropolitan Wayne County
3:47 pm - 8:38 pmORD Chicago O'Hare Intl-DFW Dallas/Fort Worth
4h 51m1 stop Minneapolis St Paul
$365Delta
Mon, Nov 9 - Thu, Nov 19
4:25 pm - 10:54 pmDFW Dallas/Fort Worth-MDW Chicago Midway
6h 29m1 stop Atlanta Hartsfield-Jackson
12:30 pm - 5:25 pmMDW Chicago Midway-DFW Dallas/Fort Worth
4h 55m1 stop Minneapolis St Paul
$365Delta
Recent direct flight deals from Dallas to Chicago
Thu, Jan 28 - Wed, Feb 3
6:00 am - 8:35 amDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
2h 35mnonstop
5:55 pm - 8:59 pmORD Chicago O'Hare Intl-DFW Dallas/Fort Worth
3h 04mnonstop
$170Frontier
Tue, Dec 15 - Fri, Dec 18
1:55 pm - 4:33 pmDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
2h 38mnonstop
3:57 pm - 6:52 pmORD Chicago O'Hare Intl-DFW Dallas/Fort Worth
2h 55mnonstop
$171Frontier
Tue, Dec 22 - Wed, Jan 6
5:05 am - 7:42 amDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
2h 37mnonstop
1:00 pm - 3:56 pmORD Chicago O'Hare Intl-DFW Dallas/Fort Worth
2h 56mnonstop
$172Frontier
Sat, Dec 5 - Sat, Dec 5
9:51 am - 12:24 pmDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
2h 33mnonstop
3:04 pm - 5:50 pmORD Chicago O'Hare Intl-DFW Dallas/Fort Worth
2h 46mnonstop
$194American Airlines
Sat, Dec 12 - Sat, Dec 12
5:25 pm - 7:59 pmDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
2h 34mnonstop
9:06 pm - 11:42 pmORD Chicago O'Hare Intl-DFW Dallas/Fort Worth
2h 36mnonstop
$194American Airlines
Wed, Dec 9 - Sat, Dec 12
8:25 pm - 10:40 pmDAL Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
6:00 am - 8:35 amMDW Chicago Midway-DAL Dallas Love Field
2h 35mnonstop
$199Southwest
Wed, Dec 2 - Wed, Dec 9
8:25 pm - 10:40 pmDAL Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
8:50 am - 11:20 amMDW Chicago Midway-DAL Dallas Love Field
2h 30mnonstop
$199Southwest
Tue, Dec 1 - Tue, Dec 8
12:39 pm - 3:06 pmDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
2h 27mnonstop
12:17 pm - 3:08 pmORD Chicago O'Hare Intl-DFW Dallas/Fort Worth
2h 51mnonstop
$199United Airlines
Tue, Dec 1 - Tue, Dec 8
8:33 pm - 11:08 pmDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
2h 35mnonstop
5:00 pm - 7:51 pmORD Chicago O'Hare Intl-DFW Dallas/Fort Worth
2h 51mnonstop
$199American Airlines
Tue, Jan 5 - Sat, Jan 9
12:25 pm - 2:55 pmDFW Dallas/Fort Worth-ORD Chicago O'Hare Intl
2h 30mnonstop
8:15 pm - 11:04 pmORD Chicago O'Hare Intl-DFW Dallas/Fort Worth
2h 49mnonstop
$225United Airlines
Booking Insights
Price, demand and travel trends for Dallas to Chicago flights
Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.
Prices
Airlines
Delays
Layovers
More
How much is a round-trip flight from Dallas to Chicago?
This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Dallas to Chicago departing in february.What is the cheapest Dallas to Chicago flight route?
KAYAK tracks online flight deals over the last 12 months and analyzes pricing trends to identify the best available fares.Dallas/Fort Worth Airport (DFW) to Chicago Midway Airport (MDW) is the cheapest Dallas to Chicago route, averaging $224 round-trip. Other Dallas to Chicago routes average $336, based on KAYAK data over the past 12 months.
What's the cheapest day of the week to fly from Dallas to Chicago?
Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Dallas to Chicago. It’s 7% cheaper than the average day, while Sunday is the most expensive, with prices 23% higher.
What’s the cheapest month to fly from Dallas to Chicago?
KAYAK internal proprietary data takes all prices for each month over the last 12 months for round-trip flights from Dallas to Chicago, removes the top 0.1% to account for outliers and then takes the median of all values for each month.•February is the cheapest month to fly from Dallas to Chicago at $188 round-trip.
•September ($319) and October ($305) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 69% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.When are flights from Dallas to Chicago the cheapest?
Flights from Dallas to Chicago are cheapest 10 weeks before departure. Booking in this window typically costs about 42% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.
Round-trip flights from Dallas to Chicago typically range from $182 to $362. The lowest price found in the past 5 days was $169, on Frontier.
Which airline is the cheapest to fly from Dallas to Chicago?
Frontier ($169) and American Airlines ($194) are the cheapest airlines to fly round-trip from Dallas to Chicago according to KAYAK data over the last 5 days.
Which airline offers the most nonstop flights between Dallas and Chicago?
American Airlines and United Airlines offer the most frequent nonstop flights from Dallas to Chicago, at 90 and 41 flights per week respectively. Southwest is another good option, operating 37 flights per week. Based on KAYAK flight data over the last 3 months.
How often are flights from Dallas to Chicago delayed?
Over the last 3 months Dallas to Chicago flights were delayed 16% of the time. Delayed flights averaged 2h 40m behind schedule.
What’s the most punctual time of day to fly from Dallas to Chicago?
Morning flights have the fewest delays. Evening departures experience delays most often.
Which day of the week has the fewest delays on Dallas to Chicago flights?
Tuesday has the fewest flight delays on the Dallas to Chicago route, at only 10% of flights delayed. Sunday has the most delays at 20%.
Which airline is the most punctual on Dallas to Chicago flights?
United Airlines is the most punctual airline on Dallas to Chicago flights. 89% of flights were on time in the past 3 months.
What’s the most popular layover airport when flying from Dallas to Chicago?
KAYAK data for 1-stop round-trips over the past 3 months. Only counts itineraries with the same layover on both legs.Fort Leonard Wood Waynesville Regional (TBN) is the most popular layover for the Dallas to Chicago route. 38% of KAYAK users who booked 1-stop round-trips over the past 3 months connected via TBN.
What is the cheapest layover airport when flying from Dallas to Chicago?
Flights via Denver Intl (DEN) offer the most affordable fares, with an average round-trip price of $186. Based on KAYAK data over the past 3 months.
Which route with a layover is the fastest from Dallas to Chicago?
Fort Leonard Wood Waynesville Regional (TBN) offers the shortest 1-stop connection from Dallas to Chicago at 4h 01m one-way, 1h 32m longer than the 2h 29m direct flight. Based on KAYAK data over the past 3 months.
When flying from Dallas to Chicago which airport offers the shortest layover?
Fort Leonard Wood Waynesville Regional (TBN) had the shortest average connection time for Dallas to Chicago layovers at 2h 22m over the past 3 months.
How many nonstop flights run daily between Dallas and Chicago?
There are 25 to 28 flights per day from Dallas to Chicago, about 186 flights per week. Monday has the most departures, with 15% of weekly flights.
What time of day do most flights depart from Dallas to Chicago?
Based on KAYAK flight schedules for the upcoming 3 months.Most nonstop flights from Dallas to Chicago depart in the morning, accounting for 43% of nonstop departures. Around 11 flights are scheduled in that window over the next three months.
Expert advice
Expert advice for your flight from Dallas to Chicago
AI-powered summary based on content written by travel experts. AI can make mistakes.
Our travel experts
Key details for Dallas to Chicago flights
Low season | February |
|---|---|
High season | June |
Cheapest flight | $106 |
When to book flights from Dallas to Chicago
Are your dates flexible? Find out the best times to travel from Dallas to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.
Flights from Dallas to Chicago: the best tips from KAYAK users' own experiences
Insights shared by verified travelers who flew the route from Dallas to Chicago
Your Dallas to Chicago flight questions, answered
Find helpful answers about this route, including flight times, airports, airlines and booking tips.
Your guide to booking Dallas to Chicago flights
Get tips on when to book, when to fly and what to know before your trip.Prefer to fly direct from Dallas to Chicago?
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Dallas to Chicago.
Direct departures
Dallas to Chicago
Monday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
Tuesday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
Wednesday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
Thursday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
Friday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
Saturday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
Sunday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
Direct returns
Chicago to Dallas
Monday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
Tuesday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
Wednesday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
Thursday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
Friday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
Saturday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
Sunday
American Airlines,Frontier,Southwest, +1 more
American Airlines,Frontier, +2 more
More options for your flight from Dallas to Chicago
Complete your trip to Chicago with a hotel stay or car rental
Other airlines flying from Dallas to Chicago
Flights from the other most popular airlines that fly from Dallas to Chicago according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.
Cabin class types available on flights from Dallas to Chicago
Cabin classes available on flights from Dallas to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Find direct flights to and from Dallas and Chicago
Flights from domestic origins to Chicago
More flights to Chicago. Prices are the lowest found on KAYAK in the last 7 days. Price and availability is not guaranteed.
Choose which airport to fly into in Chicago
Dallas to Chicago Midway Airportfrom $148
Flights to other popular destinations
The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.