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Cheap flights from Mississippi 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 Mississippi to Chicago departing on 5/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Mississippi to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
3:25 pm - 5:00 pm
MEM
-
MDW
1h 35mnonstop
Southwest Logo
9:05 pm - 10:50 pm
MDW
-
MEM
1h 45mnonstop
$97Southwest
Tue, Mar 31 - Tue, Apr 7
Southwest Logo
5:05 am - 6:40 am
MEM
-
MDW
1h 35mnonstop
Southwest Logo
4:50 pm - 9:45 pm
MDW
-
MEM
4h 55m
1 stop
$107Southwest
Tue, Mar 31 - Tue, Apr 7
Southwest Logo
6:10 am - 4:10 pm
MEM
-
MDW
10h 00m
2 stops
Southwest Logo
9:05 pm - 10:50 pm
MDW
-
MEM
1h 45mnonstop
$112Southwest
Tue, Mar 31 - Tue, Apr 7
Southwest Logo
12:20 pm - 5:05 pm
MEM
-
MDW
4h 45m
1 stop
Southwest Logo
10:15 am - 5:35 pm
MDW
-
MEM
7h 20m
2 stops
$122Southwest
Tue, Mar 31 - Tue, Apr 7
Southwest Logo
3:55 pm - 12:05 am
MEM
-
MDW
8h 10m
2 stops
Southwest Logo
2:35 pm - 9:45 pm
MDW
-
MEM
7h 10m
2 stops
$127Southwest
Tue, Mar 31 - Tue, Apr 7
Southwest Logo
8:10 am - 1:30 pm
MEM
-
MDW
5h 20m
1 stop
Southwest Logo
9:40 pm - 11:25 pm
MDW
-
MEM
1h 45mnonstop
$144Southwest
Wed, May 6 - Thu, May 7
Frontier Logo
5:54 pm - 10:21 pm
MEM
-
MDW
4h 27m
1 stop
Frontier Logo
6:00 am - 5:09 pm
MDW
-
MEM
11h 09m
1 stop
$160Frontier
Thu, Apr 9 - Sun, Apr 12
Delta Logo
6:00 am - 12:07 pm
BTR
-
MDW
6h 07m
1 stop
Delta Logo
6:00 am - 12:50 pm
MDW
-
BTR
6h 50m
1 stop
$223Delta
Wed, Apr 15 - Tue, Apr 21
Delta Logo
6:15 am - 12:02 pm
MOB
-
MDW
5h 47m
1 stop
Delta Logo
6:07 pm - 11:28 pm
MDW
-
MOB
5h 21m
1 stop
$245Delta
Tue, Mar 31 - Wed, Apr 8
Multiple Airlines Logo
7:20 pm - 11:13 pm
GPT
-
MDW
27h 53m
2 stops
Multiple Airlines Logo
5:05 am - 6:40 pm
MDW
-
GPT
13h 35m
1 stop
$363Multiple Airlines
Thu, Apr 9 - Sun, Apr 12

Southwest flights from Mississippi to Chicago Midway Airport

Our best Southwest deals on Mississippi to Chicago Midway Airport flight tickets
Southwest
Mar 31
MEM3:25 pmMemphis
1h 35m
MDW5:00 pmChicago Midway
Apr 7
MDW9:05 pmChicago Midway
1h 45m
MEM10:50 pmMemphis
$97
Southwest
Mar 31
MEM5:05 amMemphis
1h 35m
MDW6:40 amChicago Midway
Apr 7
MDW4:50 pmChicago Midway
4h 55m
1 stop
MEM9:45 pmMemphis
$107
Southwest
Mar 31
MEM6:10 amMemphis
10h 00m
2 stops
MDW4:10 pmChicago Midway
Apr 7
MDW9:05 pmChicago Midway
1h 45m
MEM10:50 pmMemphis
$112

Frontier flights from Mississippi to Chicago Midway Airport

Our best Frontier deals on Mississippi to Chicago Midway Airport flight tickets
Frontier
Apr 9
MEM5:54 pmMemphis
4h 27m
1 stop
MDW10:21 pmChicago Midway
Apr 12
MDW6:00 amChicago Midway
11h 09m
1 stop
MEM5:09 pmMemphis
$160
Frontier
Apr 9
MEM5:54 pmMemphis
4h 27m
1 stop
MDW10:21 pmChicago Midway
Apr 12
MDW6:00 amChicago Midway
11h 09m
1 stop
MEM5:09 pmMemphis
$181
Frontier
Apr 12
MEM5:54 pmMemphis
28h 25m
1 stop
MDW10:19 pmChicago Midway
Apr 19
MDW6:00 amChicago Midway
11h 42m
1 stop
MEM5:42 pmMemphis
$232

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 March 3, 2026.
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

Tue 3/31

3:25 pm-5:00 pm

Nonstop1h 35m

Chicago Midway

Tue 4/7

9:05 pm-10:50 pm

Nonstop1h 45m

$97

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Tue 3/31

5:05 am-6:40 am

Nonstop1h 35m

Chicago Midway

Tue 4/7

4:50 pm-9:45 pm

1 stop4h 55m

$107

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Tue 3/31

6:10 am-4:10 pm

2 stops10h 00m

Chicago Midway

Tue 4/7

9:05 pm-10:50 pm

Nonstop1h 45m

$112

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Tue 3/31

12:20 pm-5:05 pm

1 stop4h 45m

Chicago Midway

Tue 4/7

10:15 am-5:35 pm

2 stops7h 20m

$122

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Tue 3/31

3:55 pm-12:05 am

2 stops8h 10m

Chicago Midway

Tue 4/7

2:35 pm-9:45 pm

2 stops7h 10m

$127

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Wed 5/6

8:10 am-1:30 pm

1 stop5h 20m

Chicago Midway

Thu 5/7

9:40 pm-11:25 pm

Nonstop1h 45m

$144

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Thu 4/9

5:54 pm-10:21 pm

1 stop4h 27m

Chicago Midway

Sun 4/12

6:00 am-5:09 pm

1 stop11h 09m

$160

Baton RougeChicago

BTR - MDW

BTRMDW

Baton Rouge Ryan

Wed 4/15

6:00 am-12:07 pm

1 stop6h 07m

Chicago Midway

Tue 4/21

6:00 am-12:50 pm

1 stop6h 50m

$223

MobileChicago

MOB - MDW

MOBMDW

Mobile

Tue 3/31

6:15 am-12:02 pm

1 stop5h 47m

Chicago Midway

Wed 4/8

6:07 pm-11:28 pm

1 stop5h 21m

$245

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 4/9

7:20 pm-11:13 pm

2 stops27h 53m

Chicago Midway

Sun 4/12

5:05 am-6:40 pm

1 stop13h 35m

$363

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

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

You could potentially save up to 4% 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 $196Free CancellationRating
7.9
8,245 reviews
Search Delta flights
SouthwestPriceFrom $234Free CancellationRating
8.0
4,304 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
Valparaiso
Schererville
Munster
Crown Point
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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