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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 R 3,138. Find the lowest prices on one-way and return tickets right here.
Dallas.R 1,566 per passenger.Departing Wed, 12 Aug.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 12 Aug, arriving in Dallas Love Field.Price includes taxes and charges.From R 1,566, select.
Dallas.R 1,566 per passenger.Departing Thu, 10 Sep.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 10 Sep, arriving in Dallas Love Field.Price includes taxes and charges.From R 1,566, select.
Dallas.R 1,582 per passenger.Departing Wed, 7 Oct.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 7 Oct, arriving in Dallas Love Field.Price includes taxes and charges.From R 1,582, select.
Dallas.R 1,582 per passenger.Departing Tue, 15 Dec.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 15 Dec, arriving in Dallas Love Field.Price includes taxes and charges.From R 1,582, select.
Dallas.R 1,584 per passenger.Departing Tue, 17 Nov.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 17 Nov, arriving in Dallas Love Field.Price includes taxes and charges.From R 1,584, select.
Dallas.R 2,468 per passenger.Departing Tue, 5 Jan.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 5 Jan, arriving in Dallas Love Field.Price includes taxes and charges.From R 2,468, select.
Dallas.R 2,633 per passenger.Departing Tue, 4 May.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 4 May, arriving in Dallas Love Field.Price includes taxes and charges.From R 2,633, select.
Dallas.R 2,928 per passenger.Departing Wed, 29 Jul.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 29 Jul, arriving in Dallas Love Field.Price includes taxes and charges.From R 2,928, select.
Dallas.R 2,942 per passenger.Departing Thu, 4 Mar.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 4 Mar, arriving in Dallas Love Field.Price includes taxes and charges.From R 2,942, select.
Dallas.R 2,947 per passenger.Departing Thu, 25 Feb.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 25 Feb, arriving in Dallas Love Field.Price includes taxes and charges.From R 2,947, select.
Dallas.R 3,105 per passenger.Departing Sat, 24 Apr.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sat, 24 Apr, arriving in Dallas Love Field.Price includes taxes and charges.From R 3,105, 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 R 2,928
Aug
from R 1,566
Sep
from R 1,566
Oct
from R 1,582
Nov
from R 1,584
Dec
from R 1,582
Jan
from R 2,468
Feb
from R 2,947
Mar
from R 2,942
Apr
from R 3,105
May
from R 2,633
Jun
Find prices

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 R 1,566
Search flights

Dallas Fort Worth International

24km from central Dallas
Cheapest
from R 839
Search flights

Fort Worth

53km from central Dallas
Search flights

Chicago to Dallas: Flight information

The things to know before you go.
Cheapest flight foundR 1,566
Cheapest month to flyAugust
Average flight time2 hrs, 20 mins
Most popular airlineSouthwest Airlines
Average flights per week50

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 R 3,131. 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 20 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 50 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 September.
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 Wednesday, 9 September 2026.
Yes – the average flight time is 2 hours and 20 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

How to find the cheapest flights from Chicago Midway Airport (MDW) to Dallas Love Field Airport (DAL)

  • The cheapest price we've seen for a one-way Chicago Midway Airport to Dallas Love Field Airport flight is R 1,566. A return fare is currently R 3,131. Depending on the availability and when you book, these fares could change.

  • Score cheap tickets from MDW to DAL by booking one month ahead. According to our research, that's the sweet spot for finding a bargain.

  • The cheapest month for flights from Chicago Midway Airport to Dallas Love Field Airport is June. Use the 'Whole month' tool to see the lowest prices if you have flexible travel dates.

  • There's no need to check every day to find out if fares have dropped when you set up a Price Alert. We'll notify you as soon as there's a better deal on cheap flights from MDW to DAL.

  • Find the perfect flight for you with the help of the filters. To see the 'Cheapest,' 'Best' or 'Fastest' flights from Chicago Midway Airport to Dallas Love Field Airport, use the 'Sort by' function. You can also filter results by airline, departure and arrival times, and number of stops.

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.