$69 Cheap Flights from Memphis (MEM) to Chicago (MDW)

View $69 flight on Thu, Oct 16, 2025Opens in a new window

Popular airlines from Memphis International Airport (MEM) to Chicago Midway Airport (MDW)

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Cheap Flights from Memphis to Chicago (MEM-MDW)

Prices were available within the past 7 days and start at $69 for one-way flights and $137 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Thu, Oct 16 - Mon, Oct 20
MEM
Memphis
MDW
Chicago
$137 Roundtrip, just found
$137
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Oct 16 from Memphis to Chicago, returning Mon, Oct 20, priced at $137 just found
Southwest Airlines
Thu, Oct 16 - Mon, Oct 20
MEM
Memphis
MDW
Chicago
$147 Roundtrip, just found
$147
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Oct 16 from Memphis to Chicago, returning Mon, Oct 20, priced at $147 just found
Southwest Airlines
Thu, Oct 16 - Mon, Oct 20
MEM
Memphis
MDW
Chicago
$152 Roundtrip, just found
$152
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Oct 16 from Memphis to Chicago, returning Mon, Oct 20, priced at $152 just found
Southwest Airlines
Thu, Oct 16 - Mon, Oct 20
MEM
Memphis
MDW
Chicago
$157 Roundtrip, just found
$157
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Oct 16 from Memphis to Chicago, returning Mon, Oct 20, priced at $157 just found
Southwest Airlines
Thu, Oct 16 - Mon, Oct 20
MEM
Memphis
MDW
Chicago
$162 Roundtrip, just found
$162
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Oct 16 from Memphis to Chicago, returning Mon, Oct 20, priced at $162 just found
Southwest Airlines
Tue, Oct 7 - Thu, Oct 9
MEM
Memphis
MDW
Chicago
$167 Roundtrip, found 2 days ago
$167
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Oct 7 from Memphis to Chicago, returning Thu, Oct 9, priced at $167 found 2 days ago
Southwest Airlines
Mon, Aug 4 - Mon, Aug 11
MEM
Memphis
MDW
Chicago
$167 Roundtrip, just found
$167
Roundtrip
just found
Select Southwest Airlines flight, departing Mon, Aug 4 from Memphis to Chicago, returning Mon, Aug 11, priced at $167 just found
Southwest Airlines
Sat, Sep 6 - Tue, Sep 9
MEM
Memphis
MDW
Chicago
$168 Roundtrip, just found
$168
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Sep 6 from Memphis to Chicago, returning Tue, Sep 9, priced at $168 just found
Delta
Tue, Oct 14 - Tue, Oct 21
MEM
Memphis
MDW
Chicago
$177 Roundtrip, just found
$177
Roundtrip
just found
Select Delta flight, departing Tue, Oct 14 from Memphis to Chicago, returning Tue, Oct 21, priced at $177 just found
Southwest Airlines
Mon, Aug 4 - Mon, Aug 11
MEM
Memphis
MDW
Chicago
$177 Roundtrip, just found
$177
Roundtrip
just found
Select Southwest Airlines flight, departing Mon, Aug 4 from Memphis to Chicago, returning Mon, Aug 11, priced at $177 just found

Find the cheapest month to fly from Memphis (MEM) to Chicago (MDW)

February is typically the cheapest month to fly

From $130 - $608 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $219
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $219
Flights from Memphis (MEM) to Chicago (MDW)
Origin airport
Memphis Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$137
Distance
481 mi
Average flight time
1 hour 38 mins

Memphis to Chicago Flights

The cheapest times to fly from Memphis to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Memphis to Chicago are during the month of October. You can find some of the cheapest flights from Memphis to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Memphis to Chicago

Sunday is one of the best days to book for cheap flights from Memphis to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Memphis to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Memphis to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $69 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Memphis to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Memphis to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Memphis Intl. Airport (MEM) to Midway Intl. Airport (MDW) cost?
You can find affordable return tickets from Memphis Intl. Airport (MEM) to Midway Intl. Airport (MDW) starting at $137. Grab a seat and start your adventure. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines flight leaving MEM on July 26 2025 and touching down at MDW. The price was last updated on July 1 2025 and has not changed since.
What is the cheapest month to fly from MEM to MDW?
The cheapest flights from MEM to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Memphis Intl. Airport (MEM) to Midway Intl. Airport (MDW)?
You can fly directly from Memphis Intl. Airport (MEM) to Midway Intl. Airport (MDW) on a Southwest Airlines flight.
What is the cheapest airline that flies from MEM to MDW?
Jet off from MEM to MDW with Southwest Airlines. This carrier currently offers the cheapest one-way ticket for this route, starting from $69. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MEM on August 4 2025. Prices were last updated on July 1 2025 and have not changed since.
How many flights per day from Memphis Intl. Airport (MEM) to Midway Intl. Airport (MDW)?
On average, only 1 nonstop flight departs daily from Memphis Intl. Airport (MEM) to Midway Intl. Airport (MDW). Want more options? Use Expedia's filter tool to find flights with layovers and squeeze another destination into your itinerary.
What are the most popular departure times for flights from Memphis Intl. Airport (MEM) to Midway Intl. Airport (MDW)?
Flights between MEM and MDW tend to be busiest at 7 AM. For a more relaxed atmosphere and potentially cheaper tickets, look for a time outside the usual busy windows.
What day of the week has the most flights from MEM to MDW?
If you depart on a Friday, you'll get the largest range of options for flights from Memphis Intl. Airport (MEM) to Midway Intl. Airport (MDW).
What is the earliest flight from Memphis Intl. Airport (MEM) to Midway Intl. Airport (MDW)?
The earliest flight out of Memphis Intl. Airport (MEM) is at around 5:50AM UTC-6. Board this plane and you'll reach Midway Intl. Airport (MDW) at approximately 7:25AM UTC-6. The total time in the air is 1h 35m.
How long does it take to fly from Memphis Intl. Airport (MEM) to Midway Intl. Airport (MDW)?
It usually takes 1 hour and 38 minutes to travel the 480 mi from MEM to MDW.
What airline has the least delays from MEM to MDW?
Consider booking with Southwest Airlines if you'd like to fly straight from Memphis Intl. Airport (MEM) to Midway Intl. Airport (MDW) without any holdups. This airline has the best track record for punctuality, with an on-time score of 96%. Want to be updated if anything changes? You can keep an eye on your flight status using the Expedia App.
What is the best time to fly from Memphis Intl. Airport (MEM) to Midway Intl. Airport (MDW)?
To arrive at Midway Intl. Airport (MDW) on time, opt for a flight that leaves from Memphis Intl. Airport (MEM) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Memphis Intl. Airport (MEM)?
If you're catching a direct flight from Memphis Intl. Airport (MEM) to Chicago, you can touch down at either O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Memphis Intl. Airport (MEM) to Midway Intl. Airport (MDW) last-minute?
Waiting until just before your trip to book a flight from MEM to MDW generally means paying more. While you may come across some last-minute deals, they're not always guaranteed. Keep your travel schedule open to boost your chances of landing a bargain.
Is it cheaper to book a MEM to MDW flight and hotel package?
You'll typically save money by booking a MEM to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one convenient place. After choosing your ideal accommodations and flights, you can add extras like activities, car rentals and tours.
Can I cancel or change the date of my flight from Memphis Intl. Airport (MEM) to Midway Intl. Airport (MDW)?
You can usually reschedule or cancel your MEM to MDW flight. However, if it's been more than 24 hours since booking, additional fees may apply. Check your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find more information on our Customer Service portal.

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