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Not ready to book? to track prices.Southwest flights from Dallas Love Field Airport to Chicago Midway Airport
Our best Southwest deals on Dallas Love Field Airport to Chicago Midway Airport flight tickets
Delta flights from Dallas Love Field Airport to Chicago Midway Airport
Our best Delta deals on Dallas Love Field Airport to Chicago Midway Airport flight tickets
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Use the filters below to find and compare flights from Dallas Love Field Airport to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Sat 12/5
5:35 pm-7:50 pm
Nonstop2h 15m
Chicago Midway
Wed 12/9
8:45 pm-11:10 pm
Nonstop2h 25m
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Sat 1/9
7:10 am-9:20 am
Nonstop2h 10m
Chicago Midway
Sat 1/9
1:35 pm-4:00 pm
Nonstop2h 25m
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Wed 2/17
5:45 pm-7:55 pm
Nonstop2h 10m
Chicago Midway
Sat 2/20
8:15 pm-10:40 pm
Nonstop2h 25m
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Wed 11/25
6:55 pm-9:05 pm
Nonstop2h 10m
Chicago Midway
Wed 12/2
7:05 am-9:35 am
Nonstop2h 30m
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Wed 11/11
5:40 pm-7:55 pm
Nonstop2h 15m
Chicago Midway
Tue 12/1
8:45 pm-11:15 pm
Nonstop2h 30m
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Tue 11/10
5:40 pm-7:55 pm
Nonstop2h 15m
Chicago Midway
Wed 11/11
3:10 pm-5:35 pm
Nonstop2h 25m
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Tue 11/3
1:20 pm-5:10 pm
1 stop3h 50m
Chicago Midway
Tue 11/10
8:45 pm-11:15 pm
Nonstop2h 30m
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Sat 12/5
12:30 pm-2:45 pm
Nonstop2h 15m
Chicago Midway
Wed 12/9
3:45 pm-7:55 pm
1 stop4h 10m
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Wed 2/17
10:20 am-4:25 pm
1 stop6h 05m
Chicago Midway
Sat 2/20
9:30 am-5:50 pm
2 stops8h 20m
DallasChicago
DAL Dallas Love Field - MDW Chicago Midway
DALMDW
Dallas Love Field
Fri 1/8
6:00 am-4:50 pm
2 stops10h 50m
Chicago Midway
Sat 1/16
10:35 am-5:50 pm
1 stop7h 15m
See travel insights to Chicago from
How to get the cheapest flight ticket from Dallas Love Field Airport to Chicago Midway Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Dallas Love Field Airport and Chicago Midway Airport?
Prices are currently low for flights on this route.
Typical prices usually range from $289 to $557.The lowest price recently found on this route was $235.
What is the cheapest month to fly to Chicago Midway Airport?
The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from Dallas Love Field Airport, with most prices found around $186. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Dallas Love Field Airport during the month November is also very affordable. Most momondo users find prices during this month for around $314.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Dallas Love Field Airport. The lowest ticket price found for a Tuesday departure recently was $185. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Dallas Love Field Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $226.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Dallas Love Field Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $239 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $300. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Dallas Love Field to Chicago Midway flight route?
Fly from Dallas Love Field to Chicago Midway for the best Dallas Love Field - Chicago Midway flight prices
What cabin class options are available on Dallas Love Field Airport to Chicago Midway Airport flights?
There is only 1 cabin class available to choose from on Dallas Love Field Airport to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Dallas Love Field Airport to Chicago Midway Airport flights?
You could potentially save up to 17% on your flight if you consider stops on a Dallas Love Field Airport to Chicago Midway Airport flight.
How many flights depart from Dallas Love Field Airport to Chicago Midway Airport on average per day?
The number of flights available between Dallas Love Field Airport and Chicago Midway Airport is 3 per day as of October 2026. The most frequent departure time is 11:00AM, with 50% of daily flights leaving at noon.
How many flights depart from Dallas Love Field Airport to Chicago Midway Airport on average per week?
As of October 2026, 24 flights take off from Dallas Love Field Airport and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 33% of weekly flights taking off on this day.
When to book flights from Dallas Love Field Airport to Chicago Midway Airport
Cheap Dallas Love Field Airport to Chicago Midway Airport (DAL to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Dallas Love Field Airport to Chicago Midway Airport
Frequently asked questions about flying from Dallas Love Field Airport to Chicago Midway Airport
How far is Dallas Love Field to Chicago Midway by plane?
Chicago Midway is 793.4 mi away from Dallas Love Field. Typically, this will take 2h 10m by plane in normal conditions.
When did momondo last update prices for flights from Dallas Love Field Airport to Chicago Midway Airport?
Prices for flights from Dallas Love Field Airport to Chicago Midway Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Dallas Love Field Airport to Chicago Midway Airport?
The number of operators available for flights from Dallas Love Field Airport to Chicago Midway Airport is 1 as of October 2026.
How old do you have to be to fly from Dallas Love Field Airport to Chicago Midway Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Dallas Love Field Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Dallas Love Field Airport to Chicago Midway Airport?
Based on momondo bookings for flights between Dallas Love Field Airport and Chicago Midway Airport, the leading plane model is Boeing 737 MAX 8, making up 18.22% of the total bookings. Other popular models include Boeing 737-800 Passenger/BBJ2 (winglets) with 14.25%, Boeing 737-800 with 11.59%, and Airbus A320neo with 10.23%.
What is the most popular airline from Dallas Love Field Airport to Chicago Midway Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Dallas Love Field Airport to Chicago Midway Airport is Southwest (100% of total bookings).
Best airlines flying from Dallas Love Field Airport to Chicago Midway Airport
Compare and see reviews for airlines that fly from Dallas Love Field Airport to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $233 | Free Cancellation | Rating 7.9 4,214 reviews |
Southwest Flights From Dallas Love Field Airport to Chicago Midway Airport
Across 24 Southwest flights from Dallas Love Field Airport to Chicago Midway Airport this week, the average price was $443, with the best Southwest deals starting from $233 round-trip. 4,214 users have rated Southwest on momondo, with an average score of 7.9/10.
Traveling to a place near Chicago?
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Why should I use momondo to find a flight deal from Dallas to Chicago?
It is quick and easy to find Dallas to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.
Can I find flights from Dallas to Chicago with flexible booking policies on momondo?
All flight searches from Dallas to Chicago on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Dallas to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago from Dallas. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Dallas to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from Dallas are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.