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Cheap flights from Mississippi to Chicago from $89

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 6/30. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Mississippi to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:15 pm - 11:45 pm
MEM
-
MDW
5h 30m
1 stop
Southwest Logo
9:55 am - 11:30 am
MDW
-
MEM
1h 35mnonstop
$255Southwest
Thu, Aug 27 - Sat, Aug 29
Southwest Logo
5:20 am - 6:55 am
MEM
-
MDW
1h 35mnonstop
Southwest Logo
10:25 am - 12:00 pm
MDW
-
MEM
1h 35mnonstop
$258Southwest
Wed, Jul 1 - Sat, Jul 4
Southwest Logo
2:55 pm - 9:55 pm
MEM
-
MDW
7h 00m
2 stops
Southwest Logo
9:55 am - 11:30 am
MDW
-
MEM
1h 35mnonstop
$260Southwest
Thu, Aug 27 - Sat, Aug 29
Southwest Logo
8:15 am - 3:50 pm
MEM
-
MDW
7h 35m
2 stops
Southwest Logo
3:10 pm - 9:55 pm
MDW
-
MEM
6h 45m
2 stops
$261Southwest
Tue, Sep 8 - Thu, Sep 10
Southwest Logo
3:35 pm - 5:10 pm
MEM
-
MDW
1h 35mnonstop
Southwest Logo
9:25 pm - 11:10 pm
MDW
-
MEM
1h 45mnonstop
$264Southwest
Wed, Jul 29 - Mon, Aug 3
Multiple Airlines Logo
8:39 am - 8:30 pm
MEM
-
MDW
11h 51m
1 stop
Multiple Airlines Logo
4:45 pm - 1:13 pm
MDW
-
MEM
20h 28m
2 stops
$265Multiple Airlines
Mon, Jul 20 - Wed, Jul 22
Southwest Logo
5:20 am - 6:55 am
MEM
-
MDW
1h 35mnonstop
Southwest Logo
10:15 am - 6:00 pm
MDW
-
MEM
7h 45m
1 stop
$268Southwest
Wed, Jul 1 - Sat, Jul 4
Frontier Logo
11:51 am - 10:11 pm
MEM
-
MDW
10h 20m
1 stop
Frontier Logo
6:00 am - 10:55 am
MDW
-
MEM
4h 55m
1 stop
$269Frontier
Tue, Jun 23 - Thu, Jun 25
Delta Logo
5:03 pm - 10:25 pm
JAN
-
MDW
5h 22m
1 stop
Delta Logo
6:05 am - 10:33 am
MDW
-
JAN
4h 28m
1 stop
$287Delta
Fri, Sep 18 - Tue, Sep 22
Delta Logo
4:00 pm - 10:15 pm
GPT
-
MDW
6h 15m
1 stop
Delta Logo
4:39 pm - 8:53 pm
MDW
-
GPT
4h 14m
1 stop
$291Delta
Sat, Aug 1 - Sat, Aug 8

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Delta flights from Mississippi to Chicago Midway Airport

Our best Delta deals on Mississippi to Chicago Midway Airport flight tickets
Delta
Jul 18
MEM5:54 pmMemphis
4h 21m
1 stop
MDW10:15 pmChicago Midway
Jul 22
MDW12:41 pmChicago Midway
5h 35m
1 stop
MEM6:16 pmMemphis
$278
Delta
Jul 21
MEM5:52 pmMemphis
4h 23m
1 stop
MDW10:15 pmChicago Midway
Jul 23
MDW11:05 amChicago Midway
4h 25m
1 stop
MEM3:30 pmMemphis
$284
Delta
Sep 18
JAN5:03 pmJackson-Evers Intl
5h 22m
1 stop
MDW10:25 pmChicago Midway
Sep 22
MDW6:05 amChicago Midway
4h 28m
1 stop
JAN10:33 amJackson-Evers Intl
$287

Southwest flights from Mississippi to Chicago Midway Airport

Our best Southwest deals on Mississippi to Chicago Midway Airport flight tickets
Southwest
Aug 27
MEM6:15 pmMemphis
5h 30m
1 stop
MDW11:45 pmChicago Midway
Aug 29
MDW9:55 amChicago Midway
1h 35m
MEM11:30 amMemphis
$255
Southwest
Jul 1
MEM5:20 amMemphis
1h 35m
MDW6:55 amChicago Midway
Jul 4
MDW10:25 amChicago Midway
1h 35m
MEM12:00 pmMemphis
$258
Southwest
Aug 27
MEM2:55 pmMemphis
7h 00m
2 stops
MDW9:55 pmChicago Midway
Aug 29
MDW9:55 amChicago Midway
1h 35m
MEM11:30 amMemphis
$260

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 June 9, 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

Cheapest round-trip

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Thu 8/27

6:15 pm-11:45 pm

1 stop5h 30m

Chicago Midway

Sat 8/29

9:55 am-11:30 am

Nonstop1h 35m

$255
Quickest round-trip

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Wed 7/1

5:20 am-6:55 am

Nonstop1h 35m

Chicago Midway

Sat 7/4

10:25 am-12:00 pm

Nonstop1h 35m

$258

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Thu 8/27

2:55 pm-9:55 pm

2 stops7h 00m

Chicago Midway

Sat 8/29

9:55 am-11:30 am

Nonstop1h 35m

$260

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Tue 9/8

8:15 am-3:50 pm

2 stops7h 35m

Chicago Midway

Thu 9/10

3:10 pm-9:55 pm

2 stops6h 45m

$261

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Wed 7/29

3:35 pm-5:10 pm

Nonstop1h 35m

Chicago Midway

Mon 8/3

9:25 pm-11:10 pm

Nonstop1h 45m

$264

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Mon 7/20

8:39 am-8:30 pm

1 stop11h 51m

Chicago Midway

Wed 7/22

4:45 pm-1:13 pm

2 stops20h 28m

$265

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Wed 7/1

5:20 am-6:55 am

Nonstop1h 35m

Chicago Midway

Sat 7/4

10:15 am-6:00 pm

1 stop7h 45m

$268

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Tue 6/23

11:51 am-10:11 pm

1 stop10h 20m

Chicago Midway

Thu 6/25

6:00 am-10:55 am

1 stop4h 55m

$269

JacksonChicago

JAN - MDW

JANMDW

Jackson-Evers Intl

Fri 9/18

5:03 pm-10:25 pm

1 stop5h 22m

Chicago Midway

Tue 9/22

6:05 am-10:33 am

1 stop4h 28m

$287

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sat 8/1

4:00 pm-10:15 pm

1 stop6h 15m

Chicago Midway

Sat 8/8

4:39 pm-8:53 pm

1 stop4h 14m

$291

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 month to fly to Chicago Midway Airport?

The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from Mississippi, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Mississippi during the month January is also very affordable. Most momondo users find prices during this month for around $0.

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

Frequently asked questions about flying from Mississippi to Chicago Midway Airport

  • 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
8,394 reviews
Search Delta flights
SouthwestPriceFrom $234Free CancellationRating
7.9
4,243 reviews
Search Southwest flights

Traveling to a place near Chicago?

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