$47 Cheap flights from Love Field to Midway Intl. (DAL to MDW)

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Find The Best Dates To Fly from Love Field to Midway Intl.

Compare Flight Prices from Dallas to Chicago

Affordable Airfare Tickets from DAL to MDW Airport

The cheapest flights to Midway Intl. found within the past 7 days were $93 round trip and $47 one way. Prices and availability subject to change. Additional terms may apply.

Wed, Sep 17 - Sat, Sep 20
DAL
Dallas
MDW
Chicago
$93 Roundtrip, found 9 hours ago
$93
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Wed, Sep 17 from Dallas to Chicago, returning Sat, Sep 20, priced at $93 found 9 hours ago
Wed, Aug 27 - Wed, Sep 3
DAL
Dallas
MDW
Chicago
$103 Roundtrip, found 7 hours ago
$103
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Wed, Aug 27 from Dallas to Chicago, returning Wed, Sep 3, priced at $103 found 7 hours ago
Fri, Oct 31 - Mon, Nov 3
DAL
Dallas
MDW
Chicago
$106 Roundtrip, found 6 hours ago
$106
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Fri, Oct 31 from Dallas to Chicago, returning Mon, Nov 3, priced at $106 found 6 hours ago
Wed, Aug 27 - Wed, Sep 3
DAL
Dallas
MDW
Chicago
$113 Roundtrip, found 7 hours ago
$113
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Wed, Aug 27 from Dallas to Chicago, returning Wed, Sep 3, priced at $113 found 7 hours ago
Fri, Sep 5 - Sun, Sep 7
DAL
Dallas
MDW
Chicago
$119 Roundtrip, found 23 hours ago
$119
Roundtrip
found 23 hours ago
Select Southwest Airlines flight, departing Fri, Sep 5 from Dallas to Chicago, returning Sun, Sep 7, priced at $119 found 23 hours ago
Wed, Aug 27 - Wed, Sep 3
DAL
Dallas
MDW
Chicago
$125 Roundtrip, found 7 hours ago
$125
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Wed, Aug 27 from Dallas to Chicago, returning Wed, Sep 3, priced at $125 found 7 hours ago
Wed, Sep 17 - Sat, Sep 20
DAL
Dallas
MDW
Chicago
$128 Roundtrip, found 9 hours ago
$128
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Wed, Sep 17 from Dallas to Chicago, returning Sat, Sep 20, priced at $128 found 9 hours ago
Wed, Aug 27 - Wed, Sep 3
DAL
Dallas
MDW
Chicago
$135 Roundtrip, found 7 hours ago
$135
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Wed, Aug 27 from Dallas to Chicago, returning Wed, Sep 3, priced at $135 found 7 hours ago
Wed, Aug 27 - Wed, Sep 3
DAL
Dallas
MDW
Chicago
$138 Roundtrip, found 7 hours ago
$138
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Wed, Aug 27 from Dallas to Chicago, returning Wed, Sep 3, priced at $138 found 7 hours ago
Wed, Sep 10 - Mon, Sep 15
DAL
Dallas
MDW
Chicago
$140 Roundtrip, found 1 day ago
$140
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Sep 10 from Dallas to Chicago, returning Mon, Sep 15, priced at $140 found 1 day ago

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Save 100% on your flight
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Save 100% on your flight
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Save 100% on your flight
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
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Frequently asked questions

Can I catch a flight from DAL to Chicago Airport right now?
Be sure to go to our Covid-19 Travel Advisor to discover if there are any current quarantine requirements and travel advice reports in place in MDW when jet-setting from DAL.
Are there direct flights from Dallas Love Field to Midway Intl. Airport (MDW)?
If you'd rather fly directly from DAL to Chicago Airport, try Southwest Airlines. This airline is perfect for you if you need to travel from A to B with minimum fuss.
If I am not able to travel due to COVID-19, can I change my booking to a later date?
For more info about changing your flight to MDW, please visit our Customer Service Portal.
How long is the flight from Dallas Love Field to Chicago Airport?
Traveling from Dallas Love Field to MDW is a piece of cake as the flight usually lasts 2 hours and 9 minutes. With so little time in the air, it's highly likely that you'll hop off the plane feeling as lively as when you stepped on board.
What is the flight distance from DAL to MDW?
With only 800 mi separating DAL and MDW, there won't be much time between the fasten seat belt sign turning off and the captain advising you to prepare for landing.
What airlines fly from DAL to Midway Intl. Airport (MDW)?
Ready to fly off on your next incredible adventure? Eager to travel from Love Field Airport (DAL) to MDW as quickly as possible? Climb aboard one of the 199 direct flights offered by Southwest Airlines every month, and you'll be landing before you can ask 'Are we there yet?'
What airlines have practices regarding COVID-19 in place and use social distancing?
From the moment you enter the departure terminal to when you leave the arrivals terminal, if you're flying with Southwest Airlines, Delta or Volaris you can be sure that COVID-19 measures and social distancing rules have been adhered to. Many airlines have introduced capped capacity flights and keeping the middle seat empty.
What is the best day to buy a plane ticket?
This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that is when prices are generally at their highest.
What are the cheapest days to fly?
Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2021, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.
How far in advance can you book a flight?
Trying to figure out how early you should book your flight? It's possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Flight information from Dallas to Chicago

 

Traveling From
Love Field
Traveling To
Midway Intl.
Shortest Flight Time
2 hours 10 mins
Earliest Departure Time
6:00AM CDT
Latest Departure Time
10:45PM CDT
Lowest Flight Price
$93

Route Info

Flight path for flights from Dallas Love Field to Chicago Midway International Airport.


Origin:
DAL - Dallas Love Field
Destination:
MDW - Chicago Midway International Airport
Distance:
798.00 miles


Discover our best flights from Dallas DAL to Chicago MDW. 

With 20 airlines to choose from on Travelocity, you can easily find the best option for you. Use our filters to sort by price, compare airlines, and find the most convenient flight times. 

 

Find our best return flights from Dallas DAL to Chicago MDW at the right price  

Airfares to Chicago MDW from Dallas DAL currently cost between $93 and $140. It’s usually cheaper to book a round trip than two separate one-way flights. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way flights from Dallas DAL to Chicago MDW 

If you want to be flexible about when you return, or keep your travel options open ended, a one-way flight could be just the ticket! You’ll find one-way airfares from Dallas DAL to Chicago MDW on Travelocity starting at $47. Prices and availability subject to change. Additional terms may apply. 

 

Get to Chicago MDW from Dallas DAL quicker with direct flights. 

Get to Chicago faster, without the hassle of changing planes and moving baggage, by booking a direct flight. Expect your direct flight to MDW from DAL to take around 2 hour(s) 10 min(s).  

 

Find our cheapest airfares for flights from Dallas DAL to Chicago MDW

Find cheap flight deals by using our search filters to sort results starting with the lowest price airfares to MDW from DAL. Our Price Match Promise means if you find a lower rate on Travelocity.com or on another US-based website within 24 hours of booking, we’ll credit or refund the difference.  

 

Get our best airfare deals for your flight from Dallas DAL to Chicago MDW today 

If you’re flexible about when you travel, September is usually the cheapest month to fly from Dallas DAL to Chicago MDW. If you need to be more specific, search by date and arrival and departure times.Then, compare prices across different airlines, and sort results by lowest price first. 

 

Book flexible airline tickets for flights to Chicago MDW from Dallas DAL 

Some airlines let you change your travel dates without charging a fee. Use our ‘no change fee’ filter to see which flights to MDW from DAL have this option.  

 

Travel with confidence when you book flights to Chicago MDW from Dallas DAL with Travelocity 

We’ve secured fantastic deals with all the main airline carriers and it’s easy to compare, choose, and book with Travelocity. With 24/7 customer service and our free 'App', we’ll always keep you moving. 

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.