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101 € Cheap Flights from Dallas Love Field (DAL) to Chicago Midway (MDW)

Compare Dallas Love Field to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from Dallas Love Field to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Dallas Love Field to Chicago Midway? Find the lowest prices on one-way and return tickets right here.
Chicago.101 € per passenger.Departing Sat, 10 Jan, returning Sun, 11 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Dallas Love Field on Sat, 10 Jan, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 11 Jan, arriving in Dallas Love Field.Price includes taxes and charges.From 101 €, select.
Chicago.101 € per passenger.Departing Thu, 5 Feb, returning Mon, 9 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Dallas Love Field on Thu, 5 Feb, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 9 Feb, arriving in Dallas Love Field.Price includes taxes and charges.From 101 €, select.
Chicago.101 € per passenger.Departing Thu, 29 Jan, returning Mon, 2 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Dallas Love Field on Thu, 29 Jan, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 2 Feb, arriving in Dallas Love Field.Price includes taxes and charges.From 101 €, select.
Chicago.101 € per passenger.Departing Fri, 27 Feb, returning Sun, 1 Mar.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Dallas Love Field on Fri, 27 Feb, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 1 Mar, arriving in Dallas Love Field.Price includes taxes and charges.From 101 €, select.
Chicago.105 € per passenger.Departing Wed, 31 Dec, returning Tue, 6 Jan.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Dallas Love Field on Wed, 31 Dec, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 6 Jan, arriving in Dallas Love Field.Price includes taxes and charges.From 105 €, select.
Chicago.127 € per passenger.Departing Wed, 17 Dec, returning Wed, 31 Dec.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Dallas Love Field on Wed, 17 Dec, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 31 Dec, arriving in Dallas Love Field.Price includes taxes and charges.From 127 €, select.
Chicago.135 € per passenger.Departing Wed, 10 Dec, returning Wed, 10 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Dallas Love Field on Wed, 10 Dec, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 10 Dec, arriving in Dallas Love Field.Price includes taxes and charges.From 135 €, select.
Chicago.147 € per passenger.Departing Wed, 24 Dec, returning Mon, 5 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Dallas Love Field on Wed, 24 Dec, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 5 Jan, arriving in Dallas Love Field.Price includes taxes and charges.From 147 €, select.

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

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Dallas Love Field to Chicago Midway flights are currently cheapest in January.
Nov
from 152 €
Dec
from 127 €
Jan
from 101 €
Feb
from 101 €
Mar
from 174 €
Apr
from 233 €
May
from 240 €
Jun
from 232 €
Jul
Find prices
Aug
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Sep
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Oct
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Direct flights from Dallas Love Field to Chicago Midway

Dallas Love Field to Chicago Midway: Alternative routes

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

Dallas to Chicago: Flight information

The things to know before you go.
Cheapest flight found101 €
Cheapest month to flyFebruary
Average flight time2 hrs, 13 mins
Most popular airlineSouthwest Airlines
Average flights per week39

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

The best price we found for a return flight from Dallas Love Field to Chicago Midway is 101 €. 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 13 minutes is the average flight time from Dallas Love Field to Chicago Midway.
Southwest Airlines flies direct from Dallas Love Field to Chicago Midway.
As of November 2025, there are 39 flights per week flying from Dallas Love Field to Chicago Midway.
The cheapest month to fly from Dallas Love Field to Chicago Midway is usually February.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Dallas Love Field Airport to Chicago Midway Airport on Friday, 27 February 2026.
Yes – the average flight time is 2 hours and 13 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 Chicago Midway 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 Chicago 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 Chicago Midway.

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

  • Around 2 hours 10 minutes is how long you can expect to be in the air on a direct flight from Dallas Love Field Airport to Chicago Midway International Airport.

  • Chicago's timezone is UTC-5, which is the same as Dallas.

  • Flights from DAL to MDW start at 06:00 — the first with Southwest Airlines. The last service of the day is at 22:45 with Southwest Airlines. In total, you can choose from 33 weekly Dallas Love Field Airport to Chicago Midway International Airport flights.

  • Leave enough time to make your DAL to MDW flight. As a general rule, arrive at least two hours before international departures and an hour ahead for domestic flights.

  • Flying during a peak month like July? Major public holidays and other high seasons can mean longer lines at check-in and security. Play it safe and arrive up to four hours before an international flight and two hours before domestic departures.

  • Southwest Airlines has direct flights from Dallas Love Field Airport to Chicago Midway International Airport. Book with this popular airline, then get ready to discover the sights in Chicago — and maybe even more of United States if you have time.

  • The majority of travellers choose to fly with Southwest Airlines on this route.

  • The most punctual carrier that offers DAL to MDW flights is Southwest Airlines. Its services land as scheduled 74.66% of the time.

  • We make it a breeze to book a flight with a stopover. To see all your options for tickets from Dallas Love Field Airport to Chicago Midway International Airport, deselect 'Direct flights only.' Then, choose a flight offering a stop long enough to visit your chosen city. Stopovers between DAL and MDW include:

    • Tulsa International Airport

    • Kansas City International Airport

    • Lambert-St. Louis International Airport

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

  • The lowest price we've seen for a one-way Dallas Love Field Airport to Chicago Midway International Airport flight is 50 €. A round-trip plane ticket is currently 101 €. Depending on the availability when you book, these fares may change.

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

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

  • Stay on top of deals for cheap flights from DAL to MDW by setting up a Price Alert. We'll send you an email or notification on the app when a lower fare pops up.

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

Handy information about Dallas Love Field Airport (DAL)

  • DAL is located at 8008 Cedar Springs Road.

  • 76.03% of flights taking off from Dallas Love Field Airport reach their destination on schedule.

  • To reach Dallas Love Field Airport from central Dallas, it takes around 20 minutes if you're travelling by car. Of course, this depends on traffic conditions. It's approximately 16 kilometres from the airport to the city centre.

  • Catching public transport? You can expect a journey time of around 50 minutes.

  • Get your journey off to a leisurely start by staying near DAL. Whether you're taking an early flight from Dallas Love Field Airport to Chicago Midway International Airport or just don't want to be rushed, these stays are ideal:

Arriving at Chicago Midway International Airport (MDW)

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • MDW is located at 5700 South Cicero.

  • From Chicago Midway International Airport, Chicago is approximately 19 kilometres away. It takes around 20 minutes to get to the centre driving.

  • Getting there by public transport will take you around 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

  • July is the busiest month for flights from Dallas Love Field Airport to Chicago Midway International Airport. To escape the crowds, head to Chicago in May.

  • Lock in your flight from Dallas Love Field Airport to Chicago Midway International Airport for July if you'd like to explore Chicago during its warmest month. You can expect temperatures of between 15ºC (59ºF) and 29ºC (84ºF).

  • January sees average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Search for cheap tickets from DAL to MDW sometime around then if you'd rather travel in cooler conditions.

Explore more of United States

  • Columbus is just one of the many cities in United States waiting to be explored after you've seen Chicago. Around 451 kilometres away to the south-east, its top attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another favourite stop in United States. Experience major highlights starting with The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Plan the rest of your trip from Dallas to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.