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Cheap flights from Mississippi to Chicago from $98

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Mississippi to Chicago departing on 10/31. 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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Cheap round-trip flights

Frontier Logo
8:10 pm - 2:22 pmMEM-MDW
18h 12m2 stops
Frontier Logo
12:30 pm - 7:22 pmMDW-MEM
6h 52m1 stop
$203Frontier
Find Deal
Thu, Nov 6 - Mon, Nov 10
Delta Logo
4:30 pm - 10:14 pmMOB-MDW
5h 44m1 stop
Delta Logo
6:00 am - 12:35 pmMDW-MOB
6h 35m1 stop
$211Delta
Find Deal
Sat, Nov 8 - Sat, Nov 15
Frontier Logo
8:10 pm - 11:30 amMEM-MDW
15h 20m1 stop
Frontier Logo
12:30 pm - 7:22 pmMDW-MEM
6h 52m1 stop
$211Frontier
Find Deal
Thu, Nov 6 - Mon, Nov 10
Frontier Logo
8:10 pm - 11:16 amMEM-MDW
15h 06m1 stop
Frontier Logo
12:30 pm - 7:22 pmMDW-MEM
6h 52m1 stop
$212Frontier
Find Deal
Thu, Oct 23 - Thu, Oct 30
Southwest Logo
7:15 am - 8:50 amMEM-MDW
1h 35mnonstop
Southwest Logo
8:10 am - 9:55 amMDW-MEM
1h 45mnonstop
$214Southwest
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Sat, Nov 8 - Tue, Nov 11
Southwest Logo
7:00 am - 8:40 amMEM-MDW
1h 40mnonstop
Southwest Logo
8:00 am - 2:10 pmMDW-MEM
6h 10m1 stop
$217Southwest
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Tue, Oct 14 - Tue, Oct 21
Southwest Logo
7:00 am - 8:40 amMEM-MDW
1h 40mnonstop
Southwest Logo
8:55 pm - 10:35 pmMDW-MEM
1h 40mnonstop
$221Southwest
Find Deal
Tue, Oct 14 - Thu, Oct 16
Southwest Logo
6:00 am - 4:00 pmMEM-MDW
10h 00m2 stops
Southwest Logo
8:40 pm - 10:25 pmMDW-MEM
1h 45mnonstop
$222Southwest
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Wed, Nov 12 - Wed, Nov 12
Multiple Airlines Logo
6:48 pm - 7:34 pmMEM-MDW
24h 46m1 stop
Multiple Airlines Logo
6:20 am - 6:31 pmMDW-MEM
12h 11m2 stops
$230Multiple Airlines
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Sun, Oct 26 - Thu, Oct 30
Multiple Airlines Logo
8:10 pm - 11:16 amMEM-MDW
15h 06m1 stop
Multiple Airlines Logo
6:15 am - 11:08 pmMDW-MEM
16h 53m2 stops
$232Multiple Airlines
Find Deal
Thu, Oct 23 - Sat, Oct 25

Frontier flights from Mississippi to Chicago Midway Airport

Our best Frontier deals on Mississippi to Chicago Midway Airport flight tickets
Frontier
Nov 6
MEM8:10 pmMemphis
18h 12m
2 stops
MDW2:22 pmChicago Midway
Nov 10
MDW12:30 pmChicago Midway
6h 52m
1 stop
MEM7:22 pmMemphis
$203
Find similar
Frontier
Nov 6
MEM8:10 pmMemphis
15h 20m
1 stop
MDW11:30 amChicago Midway
Nov 10
MDW12:30 pmChicago Midway
6h 52m
1 stop
MEM7:22 pmMemphis
$211
Find similar
Frontier
Oct 23
MEM8:10 pmMemphis
15h 06m
1 stop
MDW11:16 amChicago Midway
Oct 30
MDW12:30 pmChicago Midway
6h 52m
1 stop
MEM7:22 pmMemphis
$212
Find similar

Delta flights from Mississippi to Chicago Midway Airport

Our best Delta deals on Mississippi to Chicago Midway Airport flight tickets
Delta
Nov 8
MOB4:30 pmMobile
5h 44m
1 stop
MDW10:14 pmChicago Midway
Nov 15
MDW6:00 amChicago Midway
6h 35m
1 stop
MOB12:35 pmMobile
$211
Find similar
Delta
Dec 30
MEM10:33 amMemphis
6h 47m
1 stop
MDW5:20 pmChicago Midway
Jan 6
MDW6:00 amChicago Midway
4h 56m
1 stop
MEM10:56 amMemphis
$237
Find similar
Delta
Oct 23
MEM6:30 amMemphis
5h 58m
1 stop
MDW12:28 pmChicago Midway
Oct 25
MDW4:23 pmChicago Midway
6h 33m
1 stop
MEM10:56 pmMemphis
$244
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Mississippi 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 September 25, 2025.
Use the filters below to find and compare flights from Mississippi to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Thu 11/6

8:10 pm-2:22 pm

2 stops18h 12m

Chicago Midway

Mon 11/10

12:30 pm-7:22 pm

1 stop6h 52m

$203

MobileChicago

MOB - MDW

MOBMDW

Mobile

Sat 11/8

4:30 pm-10:14 pm

1 stop5h 44m

Chicago Midway

Sat 11/15

6:00 am-12:35 pm

1 stop6h 35m

$211

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Thu 11/6

8:10 pm-11:30 am

1 stop15h 20m

Chicago Midway

Mon 11/10

12:30 pm-7:22 pm

1 stop6h 52m

$211

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Thu 10/23

8:10 pm-11:16 am

1 stop15h 06m

Chicago Midway

Thu 10/30

12:30 pm-7:22 pm

1 stop6h 52m

$212

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Sat 11/8

7:15 am-8:50 am

Nonstop1h 35m

Chicago Midway

Tue 11/11

8:10 am-9:55 am

Nonstop1h 45m

$214

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Tue 10/14

7:00 am-8:40 am

Nonstop1h 40m

Chicago Midway

Tue 10/21

8:00 am-2:10 pm

1 stop6h 10m

$217

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Tue 10/14

7:00 am-8:40 am

Nonstop1h 40m

Chicago Midway

Thu 10/16

8:55 pm-10:35 pm

Nonstop1h 40m

$221

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Wed 11/12

6:00 am-4:00 pm

2 stops10h 00m

Chicago Midway

Wed 11/12

8:40 pm-10:25 pm

Nonstop1h 45m

$222

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Sun 10/26

6:48 pm-7:34 pm

1 stop24h 46m

Chicago Midway

Thu 10/30

6:20 am-6:31 pm

2 stops12h 11m

$230

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Thu 10/23

8:10 pm-11:16 am

1 stop15h 06m

Chicago Midway

Sat 10/25

6:15 am-11:08 pm

2 stops16h 53m

$232

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 Mississippi 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 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 Mississippi. The lowest ticket price found for a Wednesday departure recently was $261. 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, Sunday is the most expensive day to depart from Mississippi because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $582.

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

Flying to Chicago Midway Airport from Mississippi in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $382 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $491. Of course, these prices can vary depending on the time of year and what airport you fly to.

Can stopping save me money on Mississippi to Chicago Midway Airport flights?

You could potentially save up to 21% on your flight if you consider stops on a Mississippi to Chicago Midway Airport flight.

Cheap Mississippi to Chicago Midway Airport flight deals and tips

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

Fastest flight time

1h 35m

Direct flights

Every day
The fastest flight from Mississippi to Chicago Midway Airport takes 1h 35m
Direct flights go from Mississippi to Chicago Midway Airport every day.
Search flight deals

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

    Prices for flights from Mississippi to Chicago Midway Airport are updated daily.

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Mississippi 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.

Best airlines flying from Mississippi to Chicago Midway Airport

Compare and see reviews for airlines that fly from Mississippi to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $116Free CancellationRating
7.9
7,973 reviews
Search Delta flights
SouthwestPriceFrom $234Free CancellationRating
8.0
4,246 reviews
Search Southwest flights

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
Portage
Lansing
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 Mississippi to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Mississippi to Chicago for you.

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

Yes. All flights to Chicago from Mississippi on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Mississippi to Chicago.

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

Yes. momondo can track prices for Mississippi 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.

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