Skyscanner home

259 € Cheap Flights from Chicago Midway to Dallas Love Field

Compare Chicago Midway to Dallas Love Field flight deals

Find the cheapest month or even day of the year to fly to Dallas Love Field

Book the best Dallas Love Field fare with no extra fees

Flight deals from Chicago Midway to Dallas Love Field

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Dallas Love Field Airport? If you want to travel next month, return fares start from 259 €. Find the lowest prices on one-way and return tickets right here.
Dallas.259 € per passenger.Departing Tue, 1 Sep, returning Thu, 1 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 1 Sep, arriving in Dallas Love Field.Inbound direct flight with Southwest Airlines departs from Dallas Love Field on Thu, 1 Oct, arriving in Chicago Midway.Price includes taxes and charges.From 259 €, select.
Dallas.259 € per passenger.Departing Tue, 4 Aug, returning Tue, 11 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 4 Aug, arriving in Dallas Love Field.Inbound direct flight with Southwest Airlines departs from Dallas Love Field on Tue, 11 Aug, arriving in Chicago Midway.Price includes taxes and charges.From 259 €, select.
Dallas.259 € per passenger.Departing Sat, 10 Oct, returning Tue, 13 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 10 Oct, arriving in Dallas Love Field.Inbound direct flight with Southwest Airlines departs from Dallas Love Field on Tue, 13 Oct, arriving in Chicago Midway.Price includes taxes and charges.From 259 €, select.
Dallas.259 € per passenger.Departing Thu, 10 Dec, returning Mon, 14 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 10 Dec, arriving in Dallas Love Field.Inbound direct flight with Southwest Airlines departs from Dallas Love Field on Mon, 14 Dec, arriving in Chicago Midway.Price includes taxes and charges.From 259 €, select.
Dallas.259 € per passenger.Departing Thu, 10 Sep, returning Mon, 14 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 10 Sep, arriving in Dallas Love Field.Inbound direct flight with Southwest Airlines departs from Dallas Love Field on Mon, 14 Sep, arriving in Chicago Midway.Price includes taxes and charges.From 259 €, select.
Dallas.259 € per passenger.Departing Wed, 19 Aug, returning Tue, 1 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 19 Aug, arriving in Dallas Love Field.Inbound direct flight with Southwest Airlines departs from Dallas Love Field on Tue, 1 Sep, arriving in Chicago Midway.Price includes taxes and charges.From 259 €, select.
Dallas.259 € per passenger.Departing Thu, 5 Nov, returning Thu, 26 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 5 Nov, arriving in Dallas Love Field.Inbound direct flight with Southwest Airlines departs from Dallas Love Field on Thu, 26 Nov, arriving in Chicago Midway.Price includes taxes and charges.From 259 €, select.
Dallas.260 € per passenger.Departing Wed, 28 Oct, returning Wed, 18 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 28 Oct, arriving in Dallas Love Field.Inbound direct flight with Southwest Airlines departs from Dallas Love Field on Wed, 18 Nov, arriving in Chicago Midway.Price includes taxes and charges.From 260 €, select.
Dallas.260 € per passenger.Departing Mon, 23 Nov, returning Thu, 7 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 23 Nov, arriving in Dallas Love Field.Inbound direct flight with Southwest Airlines departs from Dallas Love Field on Thu, 7 Jan, arriving in Chicago Midway.Price includes taxes and charges.From 260 €, select.
Dallas.260 € per passenger.Departing Thu, 8 Oct, returning Thu, 10 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 8 Oct, arriving in Dallas Love Field.Inbound direct flight with Southwest Airlines departs from Dallas Love Field on Thu, 10 Dec, arriving in Chicago Midway.Price includes taxes and charges.From 260 €, select.
Dallas.260 € per passenger.Departing Thu, 26 Nov, returning Thu, 3 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 26 Nov, arriving in Dallas Love Field.Inbound direct flight with Southwest Airlines departs from Dallas Love Field on Thu, 3 Dec, arriving in Chicago Midway.Price includes taxes and charges.From 260 €, select.
Dallas.288 € per passenger.Departing Tue, 5 Jan, returning Mon, 11 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 5 Jan, arriving in Dallas Love Field.Inbound direct flight with Southwest Airlines departs from Dallas Love Field on Mon, 11 Jan, arriving in Chicago Midway.Price includes taxes and charges.From 288 €, select.
Dallas.301 € per passenger.Departing Sat, 12 Dec, returning Sat, 2 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 12 Dec, arriving in Dallas Love Field.Inbound direct flight with Southwest Airlines departs from Dallas Love Field on Sat, 2 Jan, arriving in Chicago Midway.Price includes taxes and charges.From 301 €, select.
Dallas.306 € per passenger.Departing Wed, 10 Mar, returning Wed, 17 Mar.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Wed, 10 Mar, arriving in Dallas Love Field.Inbound indirect flight with Delta, departs from Dallas Love Field on Wed, 17 Mar, arriving in Chicago Midway.Price includes taxes and charges.From 306 €, select.
Dallas.312 € per passenger.Departing Wed, 29 Jul, returning Wed, 29 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 29 Jul, arriving in Dallas Love Field.Inbound direct flight with Southwest Airlines departs from Dallas Love Field on Wed, 29 Jul, arriving in Chicago Midway.Price includes taxes and charges.From 312 €, select.
Dallas.319 € per passenger.Departing Thu, 4 Feb, returning Fri, 5 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 4 Feb, arriving in Dallas Love Field.Inbound direct flight with Southwest Airlines departs from Dallas Love Field on Fri, 5 Feb, arriving in Chicago Midway.Price includes taxes and charges.From 319 €, select.

Find the cheapest month to fly from Chicago Midway to Dallas Love Field

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Dallas Love Field flights are currently cheapest in August.
Jul
from 312 €
Aug
from 259 €
Sep
from 259 €
Oct
from 259 €
Nov
from 259 €
Dec
from 259 €
Jan
from 288 €
Feb
from 319 €
Mar
from 306 €
Apr
from 608 €
May
from 340 €
Jun
from 344 €

Direct flights from Chicago Midway to Dallas Love Field

Chicago Midway to Dallas Love Field: Alternative routes

Compare routes from Chicago Midway to Dallas below. You may find an airport to fly into that's cheaper, faster, or easier than Dallas Love Field.

Dallas Love Field

7km from central Dallas
Closest
from 259 €
Search flights

Dallas Fort Worth International

24km from central Dallas
Cheapest
from 135 €
Search flights

Fort Worth

53km from central Dallas
Search flights

Chicago to Dallas: Flight information

The things to know before you go.
Cheapest flight found259 €
Cheapest month to flyDecember
Average flight time2 hrs, 21 mins
Most popular airlineSouthwest Airlines
Average flights per week36

Finding cheap flights from Chicago Midway to Dallas Love Field: Frequently asked questions

The best price we found for a return flight from Chicago Midway to Dallas Love Field is 259 €. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 21 minutes is the average flight time from Chicago Midway to Dallas Love Field.
Southwest Airlines flies direct from Chicago Midway to Dallas Love Field.
As of July 2026, there are 36 flights per week flying from Chicago Midway to Dallas Love Field.
The cheapest month to fly from Chicago Midway to Dallas Love Field is usually December.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Dallas Love Field Airport on Thursday, 10 December 2026.
Yes – the average flight time is 2 hours and 21 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Dallas Love Field but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Dallas is around 40 days in advance, so don’t leave your flight to the last minute.

Currently, Southwest Airlines offers the cheapest flight tickets to Dallas Love Field.

Travelling from Chicago Midway Airport (MDW) to Dallas Love Field Airport (DAL): what you need to know

  • The average duration of a direct flight from Chicago Midway Airport to Dallas Love Field Airport is 2 hours 20 minutes.

  • Chicago and Dallas are both in the UTC-6 timezone. This means there's no time difference to consider.

  • You can choose from 26 weekly Chicago Midway Airport to Dallas Love Field Airport flights. The 05:10 departure with Southwest Airlines is the earliest flight available. Southwest Airlines operates the latest service of the day at 21:10.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are travel rules to live by. Be at the airport on time to catch your MDW to DAL flight.

  • Travelling during a peak time like July? School holidays and other popular seasons can lead to longer queues at check-in and security. Play it safe and arrive up to four hours before an international flight and two hours before a domestic departure.

  • Southwest Airlines is your ticket to exploring Dallas (and maybe even some other great corners of the United States!). Check out the direct flights from Chicago Midway Airport to Dallas Love Field Airport offered by this carrier.

  • The majority of passengers choose to travel with Southwest Airlines on this route.

  • With 72.44% of services arriving as scheduled, Southwest Airlines is the most punctual carrier offering MDW to DAL flights.

  • If you want to include a stop along the way, simply uncheck 'Direct flights only' when searching for your ticket from Chicago Midway Airport to Dallas Love Field Airport. Here are the most popular stopovers between MDW and DAL:

    • Nashville Airport

    • St Louis Airport

    • Birmingham Airport

Handy information about Chicago Midway Airport (MDW)

  • You'll find MDW at 5700 South Cicero.

  • When it comes to the on-time performance of Chicago Midway Airport, data shows 76% of flights meet their scheduled arrival time.

  • To get to Chicago Midway Airport from central Chicago, it'll take around 25 minutes by car. Of course, this depends on traffic conditions. It's approximately 16 kilometres from the airport to the city centre.

  • You can expect a journey time of roughly 30 minutes on public transport.

  • Get your break off to a leisurely start by staying near MDW. Whether you've booked an early flight from Chicago Midway Airport to Dallas Love Field Airport or just don't like being rushed, these hotels are perfect:

Arriving at Dallas Love Field Airport (DAL)

When to fly to Dallas Love Field Airport (DAL)

  • June is the most popular month for flights from Chicago Midway Airport to Dallas Love Field Airport. To escape the crowds, visit Dallas in January.

  • Lock in your flight from Chicago Midway Airport to Dallas Love Field Airport for August if you want to explore Dallas during its warmest month. You can expect temperatures of between 24ºC (75ºF) and 41ºC (106ºF).

  • January sees average temperatures of between 1ºC (34ºF) and 16ºC (61ºF). Search for cheap tickets from MDW to DAL sometime then if you like travelling in cooler conditions.

Explore more of the United States

  • Houston is just one of the many places in the United States waiting to be explored after you've seen Dallas. Around 370 kilometres away to the south, well-known attractions include The Museum of Fine Arts, Houston, Beck Building, Houston Museum of Natural Science and The Menil Collection.

  • Around 402 kilometres south-west of Dallas, San Antonio is another favourite stop in the United States. Experience this destination's highlights firsthand at San Antonio River Walk, San Antonio River walk and Alamo Plaza.

Plan the rest of your trip from Chicago to Dallas

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.