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Cheap flights from Nashville to Chicago from $49

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Nashville to Chicago departing on 9/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Nashville to Chicago (BNA-MDW)

Cheap round-trip flights

Southwest Logo
5:25 am - 7:00 amBNA-MDW
1h 35mnonstop
Southwest Logo
9:45 pm - 11:10 pmMDW-BNA
1h 25mnonstop
$77Southwest
Find Deal
Thu, Sep 18 - Mon, Sep 22
Southwest Logo
7:20 am - 11:20 amBNA-MDW
4h 00m1 stop
Southwest Logo
7:55 am - 9:25 amMDW-BNA
1h 30mnonstop
$87Southwest
Find Deal
Thu, Sep 18 - Mon, Sep 22
Southwest Logo
12:10 pm - 7:00 pmBNA-MDW
6h 50m2 stops
Southwest Logo
9:45 pm - 11:10 pmMDW-BNA
1h 25mnonstop
$92Southwest
Find Deal
Sat, Sep 20 - Mon, Sep 22
Southwest Logo
7:20 am - 11:20 amBNA-MDW
4h 00m1 stop
Southwest Logo
8:15 am - 2:20 pmMDW-BNA
6h 05m1 stop
$97Southwest
Find Deal
Thu, Sep 18 - Sat, Sep 20
Southwest Logo
12:00 pm - 6:05 pmBNA-MDW
6h 05m2 stops
Southwest Logo
7:45 am - 11:25 amMDW-BNA
3h 40m1 stop
$102Southwest
Find Deal
Mon, Sep 15 - Thu, Sep 18
Southwest Logo
9:15 pm - 10:50 pmBNA-MDW
1h 35mnonstop
Southwest Logo
9:00 am - 10:30 amMDW-BNA
1h 30mnonstop
$117Southwest
Find Deal
Fri, Sep 26 - Wed, Oct 1
Southwest Logo
9:15 pm - 10:50 pmBNA-MDW
1h 35mnonstop
Southwest Logo
8:35 am - 12:55 pmMDW-BNA
4h 20m1 stop
$127Southwest
Find Deal
Fri, Sep 26 - Wed, Oct 1
Southwest Logo
1:45 pm - 3:20 pmBNA-MDW
1h 35mnonstop
Southwest Logo
9:45 pm - 11:10 pmMDW-BNA
1h 25mnonstop
$137Southwest
Find Deal
Tue, Sep 16 - Fri, Sep 19
Frontier Logo
8:14 pm - 7:11 amBNA-MDW
10h 57m1 stop
Frontier Logo
8:06 am - 7:26 pmMDW-BNA
11h 20m1 stop
$144Frontier
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Thu, Sep 25 - Sun, Sep 28
Frontier Logo
8:14 pm - 7:11 amBNA-MDW
10h 57m1 stop
Frontier Logo
8:15 am - 7:27 pmMDW-BNA
11h 12m1 stop
$145Frontier
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Thu, Sep 4 - Mon, Sep 8

Southwest flights from Nashville to Chicago Midway Airport

Our best Southwest deals on Nashville to Chicago Midway Airport flight tickets
Southwest
Sep 18
BNA5:25 amNashville Intl
1h 35m
MDW7:00 amChicago Midway
Sep 22
MDW9:45 pmChicago Midway
1h 25m
BNA11:10 pmNashville Intl
$77
Find similar
Southwest
Sep 18
BNA7:20 amNashville Intl
4h 00m
1 stop
MDW11:20 amChicago Midway
Sep 22
MDW7:55 amChicago Midway
1h 30m
BNA9:25 amNashville Intl
$87
Find similar
Southwest
Sep 20
BNA12:10 pmNashville Intl
6h 50m
2 stops
MDW7:00 pmChicago Midway
Sep 22
MDW9:45 pmChicago Midway
1h 25m
BNA11:10 pmNashville Intl
$92
Find similar

Frontier flights from Nashville to Chicago Midway Airport

Our best Frontier deals on Nashville to Chicago Midway Airport flight tickets
Frontier
Sep 25
BNA8:14 pmNashville Intl
10h 57m
1 stop
MDW7:11 amChicago Midway
Sep 28
MDW8:06 amChicago Midway
11h 20m
1 stop
BNA7:26 pmNashville Intl
$144
Find similar
Frontier
Sep 4
BNA8:14 pmNashville Intl
10h 57m
1 stop
MDW7:11 amChicago Midway
Sep 8
MDW8:15 amChicago Midway
11h 12m
1 stop
BNA7:27 pmNashville Intl
$145
Find similar
Frontier
Sep 5
BNA10:32 amNashville Intl
10h 20m
1 stop
MDW8:52 pmChicago Midway
Sep 8
MDW8:15 amChicago Midway
11h 12m
1 stop
BNA7:27 pmNashville Intl
$146
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Nashville to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 21, 2025.
Use the filters below to find and compare flights from Nashville to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Thu 9/18

5:25 am-7:00 am

Nonstop1h 35m

Chicago Midway

Mon 9/22

9:45 pm-11:10 pm

Nonstop1h 25m

$77

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Thu 9/18

7:20 am-11:20 am

1 stop4h 00m

Chicago Midway

Mon 9/22

7:55 am-9:25 am

Nonstop1h 30m

$87

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Sat 9/20

12:10 pm-7:00 pm

2 stops6h 50m

Chicago Midway

Mon 9/22

9:45 pm-11:10 pm

Nonstop1h 25m

$92

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Thu 9/18

7:20 am-11:20 am

1 stop4h 00m

Chicago Midway

Sat 9/20

8:15 am-2:20 pm

1 stop6h 05m

$97

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Mon 9/15

12:00 pm-6:05 pm

2 stops6h 05m

Chicago Midway

Thu 9/18

7:45 am-11:25 am

1 stop3h 40m

$102

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Fri 9/26

9:15 pm-10:50 pm

Nonstop1h 35m

Chicago Midway

Wed 10/1

9:00 am-10:30 am

Nonstop1h 30m

$117

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Fri 9/26

9:15 pm-10:50 pm

Nonstop1h 35m

Chicago Midway

Wed 10/1

8:35 am-12:55 pm

1 stop4h 20m

$127

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Tue 9/16

1:45 pm-3:20 pm

Nonstop1h 35m

Chicago Midway

Fri 9/19

9:45 pm-11:10 pm

Nonstop1h 25m

$137

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Thu 9/25

8:14 pm-7:11 am

1 stop10h 57m

Chicago Midway

Sun 9/28

8:06 am-7:26 pm

1 stop11h 20m

$144

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Thu 9/4

8:14 pm-7:11 am

1 stop10h 57m

Chicago Midway

Mon 9/8

8:15 am-7:27 pm

1 stop11h 12m

$145

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Nashville to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Nashville, with most prices found around $188. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Nashville during the month September is also very affordable. Most momondo users find prices during this month for around $220.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Nashville. The lowest ticket price found for a Wednesday departure recently was $219. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Nashville because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $330.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Nashville in the evening is the least expensive time of day to depart. momondo users have found prices as low as $225 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $294. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Nashville Intl to Chicago Midway flight route?

Fly from Nashville Intl to Chicago Midway for the best Nashville Intl - Chicago Midway flight prices

How far in advance should I book a flight to Chicago Midway Airport?

You are more likely to see cheaper flights to Chicago Midway Airport from Nashville when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $247 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Nashville for as low as $152 on momondo.

What cabin class options are available on Nashville Intl to Chicago Midway flights?

There are 1 cabin classes available to choose from on Nashville Intl to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

When to book flights from Nashville to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Nashville to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Nashville to Chicago Midway Airport (BNA to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Nashville to Chicago Midway Airport

Best Price Found

$102

Fastest flight time

1h 30m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Nashville in the past 72 hours is $102. The best round-trip flight deal from Nashville to Chicago Midway Airport found on momondo in the last 72 hours is $147.
The fastest flight from Nashville to Chicago Midway Airport takes 1h 30m
Direct flights go from Nashville to Chicago Midway Airport every day.
Search flight deals

  • How far is Nashville Intl to Chicago Midway by plane?

    Nashville Intl and Chicago Midway are 391.9 mi apart from one another. Flights usually cover this in 1h 35m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Nashville Intl Airport to Chicago Midway Airport?

    Prices for flights from Nashville Intl Airport to Chicago Midway Airport refresh daily.

  • How many operators does momondo search for flights from Nashville Intl Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Nashville Intl Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Nashville Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Nashville to Chicago Midway Airport?

  • What is the most popular airline from Nashville to Chicago Midway Airport?

Best airlines flying from Nashville to Chicago Midway Airport

Compare and see reviews for airlines that fly from Nashville to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $110Free CancellationRating
8.0
4,245 reviews
Search Southwest flights
DeltaPriceFrom $117Free CancellationRating
7.9
7,981 reviews
Search Delta flights

  • Southwest Flights From Nashville to Chicago Midway Airport

    Southwest flight deals from Nashville to Chicago Midway Airport start from $110 round-trip. Over the 34 Southwest flights for this route in a normal week, average airfare is usually $239 round-trip - but some users have found much cheaper deals with momondo.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Nashville to Chicago?

Finding the right flight to Chicago from Nashville is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Nashville to Chicago with flexible booking policies on momondo?

Flights from Nashville to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Nashville to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Nashville. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Nashville to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Nashville to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Chicago Midway Airport trip

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