Cheap Flights from Dallas Love Field to Chicago

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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 June.

Direct flights from Dallas Love Field to Chicago

Alternative Dallas Love Field to Chicago routes

Looking for the cheapest, fastest or easiest route from Dallas Love Field to Chicago? You could fly into the following airports instead.

Dallas to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRs24,709
Cheapest month to flyJune
Average flight time2 hrs, 19 mins
Most popular airlineSouthwest Airlines
Average flights per week67

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 Rs49,422. 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 May 2025, there are 67 flights per week flying from Dallas Love Field to Chicago.
The cheapest month to fly from Dallas Love Field to Chicago is usually May 2025.
If you're flying from Dallas Love Field Airport, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the centre of Chicago. We've found flights into this airport from Rs49,422.
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 Tuesday, 3 June 2025.
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 May, the average temperature is usually around 13°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 (DAL) to Chicago: what you need to know

  • Around 2 hours 30 minutes is how long you can expect to be travelling on a direct flight from Dallas Love Field Airport to Chicago.

  • Dallas (the location of Dallas Love Field Airport) and Chicago share the same timezone — UTC-5.

  • Dallas Love Field Airport (DAL) to Chicago Midway International Airport (MDW) is the most popular route, with 33 weekly flights to choose from. If you prefer starting your day later, the last flight from DAL to MDW is with Southwest Airlines at 22:45. Choose the first departure with Southwest Airlines at 06:00 if you want to get on your way earlier.

  • To ensure you get on your flight from DAL to Chicago, leave plenty of time for things like baggage drop and finding your gate. Turning up two hours ahead of international departures and an hour before domestic flights is the general travel rule.

  • Popular months like July or holiday times such as Thanksgiving and Christmas/New Year will mean longer waits at check-in and security. If you're travelling then, play it safe and get to the airport even earlier. Arriving two hours before domestic flights and up four hours ahead of international flights is a wise move.

  • You can book a nonstop flight from Dallas Love Field Airport to Chicago that lands at O'Hare International Airport (ORD).

  • Book your ticket with Southwest Airlines. This well-known airline offers direct flights from Dallas Love Field Airport to Chicago.

  • Once you've booked your cheap tickets from Dallas Love Field to Chicago, get your travel documents ready. A visa or passport isn't necessary since you're travelling within United States. As long as you have some other valid form of identification, like an ID card or driver's licence, you're all set.

  • The journey from central Dallas to DAL takes around 50 minutes on public transport. If you ride-share, drive or grab a cab, you'll cover the 16 kilometres in 21 minutes or so, depending on traffic conditions.

  • Want a stress-free start to your holiday? Stay near DAL. Whether you're catching an early flight from Dallas Love Field Airport to Chicago or just don't like being rushed, these hotels have you covered:

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

  • The best price we've found for a one-way ticket from Dallas Love Field Airport to Chicago is Rs24,709. The cheapest price for a return flight is Rs49,422. Keep in mind fares may change due to availability at the time of booking.

  • Book 11 months before flying. After looking at the numbers on our calendar, this is how far you'll want to book ahead to find cheap tickets from DAL to Chicago.

  • July is the cheapest month for tickets from Dallas Love Field Airport to Chicago. If you're looking to travel at a different time of year, the 'Whole month' tool will show you the lowest prices for every month.

  • Locking in a cheap ticket from DAL to Chicago is a piece of cake with Price Alerts. Simply set up one of these automatic alerts and we'll notify you when there's a better deal.

  • Tailor your travel plans with filters. Select your preferred arrival and departure times, airlines and total journey duration. You can also sort your results by 'Cheapest,' 'Best' or 'Fastest' flights from Dallas Love Field Airport to Chicago.

Airports in Chicago

O'Hare International Airport (ORD)

Chicago Midway International Airport (MDW)

Best time to go to Chicago

  • August is the busiest month to board a flight from Dallas Love Field Airport to Chicago while February is the quietest. To work out the ideal time to visit Chicago, consider whether you prefer a lively vibe or a quieter pace.

  • Book your flight from Dallas Love Field Airport to Chicago for July to visit the city during its warmest month. You can expect temperatures to range from 15ºC to 29ºC.

  • Search for cheap flights from DAL to Chicago in January if you like travelling in cooler conditions. Temperatures are at their lowest around then, ranging between -12ºC and 3ºC on average.

More about Chicago

  • After locking in your flight from Dallas Love Field to Chicago, think about where you'd like to stay in this city. Make one of these accommodation options your base for exploring Chicago:

  • Millennium Park and Art Institute of Chicago are just the start of the top-rated attractions to add to your Chicago to-do list. Keep the adventure rolling by checking out LandShark Beer Garden at Navy Pier.

Complete your Chicago trip with a car rental

  • Finding you a cheap flight from Dallas Love Field Airport to Chicago isn't our only party trick. Check out our car rentals in Chicago and explore at your own pace. We search for deals from trusted car rental providers and put them all in one place. You can instantly compare rates and then book with no fees.

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