
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $91 (Priceline) |
One-way from | $48 (Super.com) |
Popular in | March |
Cheapest in | October |
Average price | $240 |
Fly from
Fly to
Route
Depart
Return
DallasChicago
DFW - MDW
DFWMDW
Dallas/Fort Worth
Wed 5/6
5:45 am-12:43 pm
1 stop6h 58m
Chicago Midway
Wed 5/27
9:23 am-5:25 pm
1 stop8h 02m
DallasChicago
DFW - MDW
DFWMDW
Dallas/Fort Worth
Tue 4/28
4:20 pm-10:28 pm
1 stop6h 08m
Chicago Midway
Tue 5/5
6:38 pm-11:37 pm
1 stop4h 59m
DallasChicago
DFW - MDW
DFWMDW
Dallas/Fort Worth
Tue 5/5
5:49 am-12:07 pm
1 stop6h 18m
Chicago Midway
Tue 5/5
6:38 pm-11:37 pm
1 stop4h 59m
DallasChicago
DAL - ORD
DALORD
Dallas Love Field
Wed 5/13
1:55 pm-9:55 pm
2 stops8h 00m
Chicago O'Hare Intl
Wed 5/20
3:45 pm-9:25 pm
1 stop5h 40m
DallasChicago
DAL - ORD
DALORD
Dallas Love Field
Tue 5/5
7:00 am-12:50 pm
1 stop5h 50m
Chicago O'Hare Intl
Wed 5/13
2:40 pm-10:15 pm
2 stops7h 35m
DallasChicago
DAL - ORD
DALORD
Dallas Love Field
Sat 5/16
9:00 am-11:30 am
Nonstop2h 30m
Chicago O'Hare Intl
Tue 5/19
2:40 pm-10:00 pm
1 stop7h 20m
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Thu 4/16
9:45 pm-11:55 pm
Nonstop2h 10m
Chicago Midway
Mon 4/20
5:30 am-7:55 am
Nonstop2h 25m
DallasChicago
DFW - ORD
DFWORD
Dallas/Fort Worth
Tue 6/9
1:25 pm-8:31 pm
1 stop7h 06m
Chicago O'Hare Intl
Thu 6/11
5:30 am-12:50 pm
1 stop7h 20m
DallasChicago
DAL - ORD
DALORD
Dallas Love Field
Wed 5/20
7:00 am-12:50 pm
1 stop5h 50m
Chicago O'Hare Intl
Sat 5/23
1:55 pm-8:15 pm
1 stop6h 20m
DallasChicago
DFW - MDW
DFWMDW
Dallas/Fort Worth
Sat 5/16
1:29 pm-6:33 pm
1 stop5h 04m
Chicago Midway
Wed 5/20
5:10 pm-12:12 am
1 stop7h 02m
The best time to book flights from Dallas to Chicago is 78 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.
Currently, March is the cheapest month in which you can book a flight from Dallas to Chicago (average of $53). Flying from Dallas to Chicago in August is currently the most expensive (average of $111). 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.
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 54% versus a flight in the afternoon.
Travelers seeking maximum savings on their Dallas to Chicago flight should consider departing on Saturday 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 most flights from A78 to CHI are scheduled on a Friday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (18 on average).
About 18% of weekly flights between Dallas and Chicago have experienced delays in the past year, with the average delay time being 150 minutes.
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
Thursday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Over the last year, United Airlines have had the lowest number of delays on this route, with just 13% of flights being delayed.
Overall
Boarding
Food
Crew
Entertainment
Comfort
Reviews
Scott,Feb 2026
HOU - FLL
Overall
Boarding
Food
Crew
Entertainment
Comfort
Reviews
Scott,Feb 2026
HOU - FLL
Overall
Boarding
Food
Crew
Entertainment
Comfort
Reviews
Scott,Feb 2026
HOU - FLL
Overall
Boarding
Food
Crew
Entertainment
Comfort
Reviews
Scott,Feb 2026
HOU - FLL
Overall
Boarding
Food
Crew
Entertainment
Comfort
Reviews
Scott,Feb 2026
HOU - FLL
Overall
Boarding
Food
Crew
Entertainment
Comfort
Reviews
Scott,Feb 2026
HOU - FLL
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.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$64 | Average$178 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$64 | Average$149 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$89 | Average$215 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$145 | Average$288 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$154 | Average$294 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$157 | Average$293 | FlexibilityNo cancel fee | On-time71% |