Cheap flights from Dallas to Chicago Midway

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

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Flight deals from Dallas to Chicago Midway

Looking for a cheap last-minute deal or the best round-trip flight from Dallas to Chicago Midway Airport? If you want to travel next month, round-trip fares start from $184. Find the lowest prices on one-way and round-trip tickets right here.

Chicago.$149 per passenger.Departing Sat, Jun 27, returning Fri, Jul 3.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Dallas Fort Worth International on Sat, Jun 27, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Fri, Jul 3, arriving in Dallas Fort Worth International.Price includes taxes and charges.From $149, select.

Chicago.$157 per passenger.Departing Sat, Oct 17, returning Sun, Oct 25.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Dallas Fort Worth International on Sat, Oct 17, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Sun, Oct 25, arriving in Dallas Fort Worth International.Price includes taxes and charges.From $157, select.

Chicago.$157 per passenger.Departing Sat, Aug 8, returning Thu, Aug 13.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Dallas Fort Worth International on Sat, Aug 8, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Thu, Aug 13, arriving in Dallas Fort Worth International.Price includes taxes and charges.From $157, select.

Chicago.$161 per passenger.Departing Sat, Sep 26, returning Sat, Oct 3.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Dallas Fort Worth International on Sat, Sep 26, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Sat, Oct 3, arriving in Dallas Fort Worth International.Price includes taxes and charges.From $161, select.

Chicago.$165 per passenger.Departing Fri, Aug 28, returning Fri, Sep 4.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Dallas Fort Worth International on Fri, Aug 28, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Fri, Sep 4, arriving in Dallas Fort Worth International.Price includes taxes and charges.From $165, select.

Chicago.$165 per passenger.Departing Fri, Oct 30, returning Mon, Nov 2.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Dallas Fort Worth International on Fri, Oct 30, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Mon, Nov 2, arriving in Dallas Fort Worth International.Price includes taxes and charges.From $165, select.

Chicago.$165 per passenger.Departing Fri, Nov 6, returning Fri, Nov 13.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Dallas Fort Worth International on Fri, Nov 6, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Fri, Nov 13, arriving in Dallas Fort Worth International.Price includes taxes and charges.From $165, select.

Chicago.$165 per passenger.Departing Thu, Sep 10, returning Sun, Sep 13.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Dallas Fort Worth International on Thu, Sep 10, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Sun, Sep 13, arriving in Dallas Fort Worth International.Price includes taxes and charges.From $165, select.

Chicago.$184 per passenger.Departing Sat, Jun 13, returning Fri, Jun 19.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Dallas Fort Worth International on Sat, Jun 13, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Fri, Jun 19, arriving in Dallas Fort Worth International.Price includes taxes and charges.From $184, select.

Chicago.$184 per passenger.Departing Thu, Jul 23, returning Sat, Jul 25.Round-trip flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from Dallas Fort Worth International on Thu, Jul 23, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Sat, Jul 25, arriving in Dallas Fort Worth International.Price includes taxes and charges.From $184, select.

Chicago.$186 per passenger.Departing Sat, Jul 25, returning Sat, Aug 8.Round-trip flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from Dallas Fort Worth International on Sat, Jul 25, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Sat, Aug 8, arriving in Dallas Fort Worth International.Price includes taxes and charges.From $186, select.

Chicago.$194 per passenger.Departing Mon, Jul 20, returning Sat, Jul 25.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Dallas Fort Worth International on Mon, Jul 20, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Sat, Jul 25, arriving in Dallas Fort Worth International.Price includes taxes and charges.From $194, select.

Chicago.$197 per passenger.Departing Mon, Jul 27, returning Sat, Aug 8.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Dallas Fort Worth International on Mon, Jul 27, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Sat, Aug 8, arriving in Dallas Fort Worth International.Price includes taxes and charges.From $197, select.

Chicago.$225 per passenger.Departing Fri, May 29, returning Fri, Jun 12.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Dallas Fort Worth International on Fri, May 29, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Fri, Jun 12, arriving in Dallas Fort Worth International.Price includes taxes and charges.From $225, select.

Chicago.$227 per passenger.Departing Thu, May 28, returning Fri, May 29.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Dallas Fort Worth International on Thu, May 28, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Fri, May 29, arriving in Dallas Fort Worth International.Price includes taxes and charges.From $227, select.

Chicago.$267 per passenger.Departing Fri, Aug 21, returning Fri, Oct 2.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Dallas Fort Worth International on Fri, Aug 21, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Fri, Oct 2, arriving in Dallas Fort Worth International.Price includes taxes and charges.From $267, select.

Find the cheapest month to fly from Dallas to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Dallas to Chicago Midway flights are currently cheapest in August.

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Direct flights from Dallas to Chicago Midway

Dallas to Chicago Midway: Alternative routes

Compare routes from Dallas 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 found	$149
Cheapest month to fly	June
Average flight time	2 hrs, 18 mins
Most popular airline	Southwest Airlines
Average flights per week	51

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

How much are round-trip flights from Dallas to Chicago Midway?

The best price we found for a round-trip flight from Dallas to Chicago Midway is $149. 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.

How long does it take to fly from Dallas to Chicago Midway?

2 hours and 17 minutes is the average flight time from Dallas to Chicago Midway.

Which airlines fly direct from Dallas to Chicago Midway?

Southwest Airlines, Frontier Airlines and Volaris fly direct from Dallas to Chicago Midway.

How many flights are there a week from Dallas to Chicago Midway?

There are 51 flights per week flying from Dallas to Chicago Midway, as of May 2026.

When is the cheapest time to fly from Dallas to Chicago Midway?

The cheapest month to fly from Dallas to Chicago Midway is usually June.

Which upcoming date is cheapest to fly from Dallas to Chicago Midway Airport on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Dallas to Chicago Midway Airport on Saturday, June 27, 2026.

Can I get a direct flight from Dallas to Chicago Midway Airport?

Yes – the average flight time is 2 hours and 17 minutes.

How can I find the best flight deal to Chicago Midway?

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.

When is the best time to book flights to Chicago?

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.

Which is the cheapest airline to fly with from Dallas to Chicago Midway?

The cheapest airline that flies to Chicago Midway is Frontier Airlines.

Traveling from Dallas to Chicago Midway International Airport (MDW): What you need to know

Kick off your travels at one of Dallas's main airports, Dallas Fort Worth International Airport (DFW) or Dallas Love Field (DAL). Explore your options for booking a flight from Dallas to Chicago Midway International Airport (MDW) departing from either of these.
The average length of a direct Dallas to Chicago Midway International Airport flight is 2 hours 20 minutes.
Chicago's timezone is UTC-6, which is the same as Dallas. Chicago Midway International Airport is located in Chicago.
To ensure you catch your flight from Dallas to MDW, allow plenty of time to check in and drop off your luggage. Turning up two hours ahead of international departures and one hour before domestic flights is the general travel rule.
If you're traveling during a popular month like July, make your way to the airport even earlier. It's wise to arrive up to four hours before international flights and two hours ahead of a domestic departure. Check-in and security lines are longer during vacation periods like Thanksgiving and spring break.

Airports in Dallas

Dallas Fort Worth International Airport (DFW)

You can find a direct flight from Dallas to Chicago Midway International Airport (MDW) departing from Dallas Fort Worth International Airport (DFW).
When jetting out of DFW, you can take a direct flight from Dallas to Chicago Midway International Airport with Frontier Airlines.
Frontier Airlines is the airline with the highest number of bookings for flights from DFW to MDW.
Among carriers operating on this route, Frontier Airlines is the most consistent for on-time landings.
The journey from central Dallas to DFW takes about 1 hour on public transport. If you drive, ride-share or take a cab, you'll cover the 32 kilometers in 25 minutes or so, depending on traffic conditions.
Want an easy start to your trip? Stay near Dallas Fort Worth International Airport. Whether you've booked an early flight from Dallas to Chicago Midway International Airport or aren't a fan of being rushed, these hotels are the ideal choice:
72% of flights departing from Dallas Fort Worth International Airport arrive at their destination on time.
You'll find DFW at 2400 Aviation Dr.

Dallas Love Field (DAL)

You can book a direct Dallas to Chicago Midway International Airport (MDW) plane ticket out of Dallas Love Field (DAL). Work out whether departing from DAL makes the most sense for you.
Southwest Airlines offers direct flights from Dallas to MDW out of DAL. Book your favorite seat and reach your destination in one go.
Southwest Airlines is the most popular choice for travelers flying from DAL to MDW.
With 71.53% of its services arriving as scheduled, Southwest Airlines is the most punctual carrier flying between Dallas Love Field and Chicago Midway International Airport.
DAL is around 13 kilometers from central Dallas. It'll take you 20 minutes or so to get to the airport if you're driving from the city center. Public transport takes roughly 45 minutes.
Flying out early in the morning? Think about staying at one of these accommodation options near Dallas Love Field the day before your Dallas to MDW flight:
74% of flights taking off from Dallas Love Field arrive according to schedule.
The street address for DAL is 8008 Cedar Springs Road.

About Chicago Midway International Airport (MDW)

The last thing you need is a long journey to your hotel if you're arriving on a late flight from Dallas to Chicago Midway International Airport. Make yourself comfy at one of these accommodation options near MDW instead:
Booking your vehicle around four weeks ahead of your Dallas to Chicago Midway International Airport flight can help you score a better rate.
The street address for MDW is 5700 South Cicero.

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

Chicago Midway International Airport is around 16 kilometers from central Chicago. It takes around 25 minutes or so to get to the city by car.
Traveling on public transport will take you around 30 minutes.

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

Right now, $74 is the best price we've found for a one-way ticket from Dallas to Chicago Midway International Airport. The cheapest price for a return flight is $149. Remember fares may change due to availability at the time of booking.
Book two months before you want to fly. Pricing trends show that this is the ideal window for finding cheap flights from Dallas to MDW.
July is when you're most likely to find a good deal on a Dallas to Chicago Midway International Airport ticket. If you're looking to travel at a different time of year, the 'Whole month' tool will give you the lowest prices for each month.
Locking in a cheap plane ticket from Dallas to MDW couldn't be easier with Price Alerts. Simply create one of these automatic alerts and we'll get in touch when prices go down.
Find a cheap flight from Dallas to Chicago Midway International Airport by using the search filters. Select your ideal times, number of stops and airlines, then sort the results by 'Cheapest' for the best deals.

The best time to fly from Dallas to Chicago Midway International Airport (MDW)

It's time to work out when to book your flight from Dallas to Chicago Midway International Airport (MDW). July is the most popular month to visit Chicago. If you like things a bit more low-key, think about going in November.
Before locking in your Dallas to MDW plane ticket, consider the kind of weather you prefer. July is the warmest month in Chicago, with temperatures ranging from 16ºC (61ºF) to 28ºC (82ºF).
Look for cheap tickets from Dallas to Chicago Midway International Airport in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

After booking your flight from Dallas to Chicago Midway International Airport, find a hotel that's got location and comfort covered. Make one of these accommodation options your base for exploring Chicago:
Your Chicago trip won't be complete without checking out the sights. Major attractions that are worth your time include Millennium Park, Art Institute of Chicago and Willis Tower.

Explore more of the United States

Indianapolis is just one of the many cities in the United States waiting to be discovered once you've taken in the sights of Chicago. Around 257 kilometers away to the southeast, popular attractions include Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.
Milwaukee is another must-experience destination in the United States and is around 137 kilometers north of Chicago. No trip is complete without experiencing Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo.