Cheap Flights from Dallas Love Field (DAL) to Chicago (CHIA)

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Flight deals from Dallas Love Field to Chicago

Looking for a cheap last-minute deal or the best return flight from Dallas Love Field to Chicago? Find the lowest prices on one-way and return tickets right here.

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

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 flights are currently cheapest in April.

Direct flights from Dallas Love Field to Chicago

Dallas to Chicago: Flight information

The things to know before you go.
Cheapest flight found£106
Cheapest month to flyApril
Average flight time2 hrs, 20 mins
Most popular airlineSouthwest Airlines
Average flights per week60

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

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Dallas Love Field to Chicago is £106. 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 19 minutes is the average flight time from Dallas Love Field to Chicago.
Southwest Airlines flies direct from Dallas Love Field to Chicago.
As of February 2026, there are 60 flights per week flying from Dallas Love Field to Chicago.
The cheapest month to fly from Dallas Love Field to Chicago is usually April.
If you're flying from Dallas Love Field Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 15.8 miles away from the centre of Chicago. We've found flights into this airport from £106.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Dallas Love Field Airport to Chicago on Saturday, 18 April 2026.
Yes – the average flight time is 2 hours and 19 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 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.
In February, the average temperature is usually around -2°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Southwest Airlines offers the cheapest flight tickets to Chicago.

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

  • Expect to be in the air for 2 hours 25 minutes. That's the average journey time for a direct flight from Dallas Love Field Airport to Chicago.

  • Chicago's timezone is UTC-5, which is the same as Dallas (the location of Dallas Love Field Airport).

  • With 27 weekly flights between the two airports, Dallas Love Field Airport (DAL) to Chicago Midway International Airport (MDW) is the most popular route. Southwest Airlines operates the earliest flight at 06:00. If you'd like to make the most of your day before leaving, the latest flight from DAL to MDW is with Southwest Airlines at 22:45.

  • Leave plenty of time to get on your DAL to Chicago flight. As a general rule, turn up at least two hours before international departures and an hour ahead for domestic flights.

  • Planning to travel during a peak period like a bank holiday? Expect longer lines at check-in and security. Play it safe and arrive up to four hours before international flights and two hours ahead of domestic departures.

  • Begin your journey at DAL and fly straight to O'Hare International Airport (ORD). That's where you can expect to land when searching for Dallas Love Field Airport to Chicago tickets.

  • Southwest Airlines is a popular carrier that offers direct flights from Dallas Love Field Airport to Chicago.

  • Located around 6 miles from the centre of Dallas, DAL can be reached in about 20 minutes by car (depending on traffic). Travelling on public transport will take roughly 50 minutes.

  • Searching for a hotel near DAL? If you're catching an early flight from Dallas Love Field Airport to Chicago, these accommodation options will put you moments from check-in:

  • 76.03% of flights that leave from Dallas Love Field Airport make it to their destination on time.

  • DAL's address is 8008 Cedar Springs Road.

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

  • The lowest price we've found for a one-way Dallas Love Field Airport to Chicago flight is £53. The cheapest price for a return flight is £106. Bear in mind fares can change due to demand at the time of booking.

  • Get cheap flights from DAL to Chicago by booking three months ahead. Based on our research, that's the best time for landing a bargain.

  • Organise your trip for July. That's the best month for scoring a bargain on Dallas Love Field Airport to Chicago tickets. If you're flexible with your dates, use the 'Whole month' tool to access the cheapest price across every month.

  • Never miss a deal on cheap flights from DAL to Chicago by setting up a Price Alert. You'll get an email or push notification on the app when a lower fare pops up.

  • Save money on your flight from Dallas Love Field Airport to Chicago with the help of our filters. Select your preferred times, number of stops and airlines, then sort the results by 'Cheapest' for the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) is around 25 miles from the centre of Chicago. If you're catching a cab or a ride-share, the drive takes about 35 minutes.

  • When travelling by public transport, expect a journey time of about 55 minutes.

  • If you're coming in on a late flight from Dallas Love Field Airport to Chicago, nothing beats the convenience of staying near the terminal. Pick up your bags from the carousel and then be showered and snoozing not long after at one of these hotels near ORD:

  • Travel at your own speed with an O'Hare International Airport rental car. Pick up a set of wheels from Routes Car Rentals, Dollar or Budget and find adventure across Chicago and beyond.

  • Lock in the best deal by booking your vehicle from O'Hare International Airport around four weeks ahead of your flight from DAL to Chicago.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Once your flight from Dallas Love Field Airport to Chicago has touched down, you can make your way to the city centre in about 20 minutes by car. Central Chicago is roughly 12 miles from Chicago Midway International Airport (MDW).

  • Public transport will get you there in about 45 minutes.

  • Place the 'Do not disturb' sign on your door and rest at a hotel close to MDW. Here are a few options where you can settle in after your DAL to Chicago flight:

  • The quickest way to get to where you're going is with a Chicago Midway International Airport rental car. Collect a set of wheels from Dollar, Hertz or Budget and set off in the blink of an eye.

  • Snap up the best price by booking your ride from MDW four weeks ahead of time. You'll also have access to a greater selection of vehicles.

  • You'll find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is around 85 miles from the centre of Chicago. It takes about 1 hour 25 minutes to reach the city centre in a ride-share or cab once you've stepped off your flight from Dallas Love Field Airport to Chicago.

  • The journey takes roughly 4 hours 15 minutes using public transport.

  • Book a hotel close to RFD and get from baggage claim to your bed in a snap. Whether you're coming in on a late DAL to Chicago flight or just want a stress-free arrival, these stays will have you settling in quickly:

  • Take control of the next leg of your trip by picking up a Chicago Rockford International Airport rental car. Budget, Alamo and National are reliable rental providers.

  • Booking at least a few weeks in advance of your flight from Dallas Love Field Airport to Chicago is a good move. As well as better prices, you'll have a wider selection of vehicle makes and models at RFD.

  • Chicago Rockford International Airport's street address is 2 Airport Cir.

Best time to go to Chicago

  • Travel to Chicago during high season if you like a lively atmosphere, but remember that hotel prices may be higher. Alternatively, book your flights from Dallas Love Field Airport to Chicago in the off-season when prices are cheaper and it's quieter.

  • Lock in a Dallas Love Field Airport to Chicago plane ticket with a departure in July to experience the city during its warmest month. You can expect temperatures to range from 15ºC (59ºF) to 29ºC (84ºF).

  • If you want to travel in cooler conditions, look for a cheap ticket from DAL to Chicago in January when temperatures average between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

  • When it comes to looking for somewhere to rest your head, you'll find the most popular stays in Chicago right here. Check out these options as soon as you've booked your flight from Dallas Love Field Airport to Chicago:

  • There are so many things to explore in this city it can be hard to figure out where to start. Art Institute of Chicago, Millennium Park and LandShark Beer Garden at Navy Pier are top attractions which should feature on any well-planned Chicago itinerary.

Explore more of United States

  • Columbus is just one of the many places in United States waiting to be discovered after you've experienced Chicago. Around 280 miles away to the south-east, popular attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Around 160 miles south-east of Chicago, Indianapolis is another essential stop in United States. Start your sightseeing at The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

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