
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $100 (Trip.com) |
One-way from | $51 (Trip.com) |
Popular in | May |
Cheapest in | December |
Average price | $235 |
Fly from
Fly to
Route
Depart
Return
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Mon 4/27
9:45 pm-11:55 pm
Nonstop2h 10m
Chicago Midway
Mon 6/1
7:20 am-9:45 am
Nonstop2h 25m
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Thu 5/7
6:20 am-8:30 am
Nonstop2h 10m
Chicago Midway
Thu 5/14
12:45 pm-4:55 pm
1 stop4h 10m
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Mon 5/4
6:20 am-8:30 am
Nonstop2h 10m
Chicago Midway
Mon 5/4
10:20 am-2:05 pm
1 stop3h 45m
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Wed 6/10
7:50 pm-10:00 pm
Nonstop2h 10m
Chicago Midway
Tue 6/16
5:05 am-7:20 am
Nonstop2h 15m
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Sat 5/9
12:40 pm-4:50 pm
1 stop4h 10m
Chicago Midway
Mon 5/11
12:45 pm-4:55 pm
1 stop4h 10m
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Tue 4/28
1:30 pm-4:50 pm
1 stop3h 20m
Chicago Midway
Sat 5/2
8:10 am-2:45 pm
2 stops6h 35m
DallasChicago
DFW - MDW
DFWMDW
Dallas/Fort Worth
Wed 6/3
7:00 am-1:19 pm
1 stop6h 19m
Chicago Midway
Sat 6/6
5:30 pm-12:12 am
1 stop6h 42m
DallasChicago
DFW - MDW
DFWMDW
Dallas/Fort Worth
Sat 5/2
4:20 pm-10:28 pm
1 stop6h 08m
Chicago Midway
Tue 5/5
12:52 pm-7:04 pm
1 stop6h 12m
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Sat 5/9
12:30 pm-5:10 pm
1 stop4h 40m
Chicago Midway
Sun 5/10
6:55 am-9:25 am
Nonstop2h 30m
DallasChicago
DAL - MDW
DALMDW
Dallas Love Field
Fri 6/12
10:50 pm-1:00 am
Nonstop2h 10m
Chicago Midway
Tue 6/16
5:05 am-7:20 am
Nonstop2h 15m
Booking 72 days in advance of your planned departure date is, on average, the best time to get cheap flights from Dallas to Chicago Midway Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Currently, January is the cheapest month in which you can book a flight from Dallas to Chicago Midway Airport (average of $63). Flying from Dallas to Chicago Midway Airport in May is currently the most expensive (average of $122). 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 Midway Airport, 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 13% versus a flight in the afternoon.
Travelers seeking maximum savings on their Dallas to Chicago Midway Airport 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.
About 19% of weekly flights between Dallas and Chicago have experienced delays in the past year, with the average delay time being 147 minutes.
Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.
Wednesday 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, Frontier have had the lowest number of delays on this route, with just 19% of flights being delayed.
Entertainment
Crew
Food
Boarding
Comfort
Overall
Reviews
Scott,Feb 2026
HOU - FLL
Entertainment
Crew
Food
Boarding
Comfort
Overall
Reviews
Scott,Feb 2026
HOU - FLL
Entertainment
Crew
Food
Boarding
Comfort
Overall
Reviews
Scott,Feb 2026
HOU - FLL
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$77 | Average$184 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$145 | Average$295 | FlexibilityNo cancel fee | On-time63% |