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Cheap flights from Mississippi to Chicago from $55

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 12/8. 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 Mississippi to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:55 pm - 1:16 pmGPT-ORD
17h 21m1 stop
Multiple Airlines Logo
7:20 am - 7:15 pmORD-GPT
11h 55m1 stop
$208Multiple Airlines
Find Deal
Thu, Dec 4 - Thu, Dec 11
Delta Logo
7:17 pm - 11:47 pmMOB-MDW
4h 30m1 stop
Delta Logo
6:00 am - 12:40 pmMDW-MOB
6h 40m1 stop
$211Delta
Find Deal
Wed, Dec 10 - Sat, Dec 13
American Airlines Logo
7:27 pm - 9:29 pmMEM-ORD
2h 02mnonstop
American Airlines Logo
10:04 pm - 11:59 pmORD-MEM
1h 55mnonstop
$216American Airlines
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Fri, Dec 5 - Sun, Dec 7
Southwest Logo
1:25 pm - 7:30 pmMEM-MDW
6h 05m2 stops
Southwest Logo
6:20 am - 12:50 pmMDW-MEM
6h 30m1 stop
$216Southwest
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Fri, Dec 5 - Sun, Dec 7
American Airlines Logo
5:15 am - 1:34 pmMEM-ORD
8h 19m1 stop
American Airlines Logo
1:32 pm - 3:25 pmORD-MEM
1h 53mnonstop
$217American Airlines
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Tue, Dec 9 - Wed, Dec 10
Southwest Logo
1:25 pm - 7:20 pmMEM-MDW
5h 55m1 stop
Southwest Logo
8:15 am - 10:00 amMDW-MEM
1h 45mnonstop
$220Southwest
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Mon, Dec 8 - Wed, Dec 24
Frontier Logo
3:27 pm - 10:43 pmMEM-MDW
7h 16m1 stop
Frontier Logo
6:05 am - 5:41 pmMDW-MEM
11h 36m1 stop
$221Frontier
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Thu, Nov 20 - Tue, Nov 25
Frontier Logo
7:59 pm - 12:10 amMEM-ORD
28h 11m1 stop
Frontier Logo
7:57 pm - 7:04 pmORD-MEM
23h 07m2 stops
$230Frontier
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Wed, Nov 26 - Sun, Nov 30
Spirit Airlines Logo
10:07 am - 10:50 pmMEM-ORD
12h 43m2 stops
Spirit Airlines Logo
7:10 am - 6:47 pmORD-MEM
11h 37m2 stops
$252Spirit Airlines
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Wed, Dec 3 - Wed, Dec 10
Spirit Airlines Logo
10:07 am - 10:50 pmMEM-ORD
12h 43m2 stops
Spirit Airlines Logo
7:10 am - 6:47 pmORD-MEM
11h 37m2 stops
$253Spirit Airlines
Find Deal
Wed, Dec 3 - Thu, Dec 4

Frontier flights from Mississippi to Chicago

Our best Frontier deals on Mississippi to Chicago flight tickets
Frontier
Nov 20
MEM3:27 pmMemphis
7h 16m
1 stop
MDW10:43 pmChicago Midway
Nov 25
MDW6:05 amChicago Midway
11h 36m
1 stop
MEM5:41 pmMemphis
$221
Find similar
Frontier
Nov 26
MEM7:59 pmMemphis
28h 11m
1 stop
ORD12:10 amChicago O'Hare Intl
Nov 30
ORD7:57 pmChicago O'Hare Intl
23h 07m
2 stops
MEM7:04 pmMemphis
$230
Find similar
Frontier
Nov 20
MEM3:27 pmMemphis
7h 16m
1 stop
MDW10:43 pmChicago Midway
Nov 23
MDW6:05 amChicago Midway
8h 15m
1 stop
MEM2:20 pmMemphis
$231
Find similar

American Airlines flights from Mississippi to Chicago

Our best American Airlines deals on Mississippi to Chicago flight tickets
American Airlines
Dec 5
MEM7:27 pmMemphis
2h 02m
ORD9:29 pmChicago O'Hare Intl
Dec 7
ORD10:04 pmChicago O'Hare Intl
1h 55m
MEM11:59 pmMemphis
$216
Find similar
American Airlines
Dec 9
MEM5:15 amMemphis
8h 19m
1 stop
ORD1:34 pmChicago O'Hare Intl
Dec 10
ORD1:32 pmChicago O'Hare Intl
1h 53m
MEM3:25 pmMemphis
$217
Find similar
American Airlines
Nov 26
MEM5:03 pmMemphis
5h 53m
1 stop
ORD10:56 pmChicago O'Hare Intl
Dec 3
ORD8:26 amChicago O'Hare Intl
1h 55m
MEM10:21 amMemphis
$221
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momondo Fare Finder

 
Customize your flight search to find flights from Mississippi to Chicago 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 November 6, 2025.
Use the filters below to find and compare flights from Mississippi to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Thu 12/4

7:55 pm-1:16 pm

1 stop17h 21m

Chicago O'Hare Intl

Thu 12/11

7:20 am-7:15 pm

1 stop11h 55m

$208

MobileChicago

MOB - MDW

MOBMDW

Mobile

Wed 12/10

7:17 pm-11:47 pm

1 stop4h 30m

Chicago Midway

Sat 12/13

6:00 am-12:40 pm

1 stop6h 40m

$211

MemphisChicago

MEM - ORD

MEMORD

Memphis

Fri 12/5

7:27 pm-9:29 pm

Nonstop2h 02m

Chicago O'Hare Intl

Sun 12/7

10:04 pm-11:59 pm

Nonstop1h 55m

$216

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Fri 12/5

1:25 pm-7:30 pm

2 stops6h 05m

Chicago Midway

Sun 12/7

6:20 am-12:50 pm

1 stop6h 30m

$216

MemphisChicago

MEM - ORD

MEMORD

Memphis

Tue 12/9

5:15 am-1:34 pm

1 stop8h 19m

Chicago O'Hare Intl

Wed 12/10

1:32 pm-3:25 pm

Nonstop1h 53m

$217

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Mon 12/8

1:25 pm-7:20 pm

1 stop5h 55m

Chicago Midway

Wed 12/24

8:15 am-10:00 am

Nonstop1h 45m

$220

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Thu 11/20

3:27 pm-10:43 pm

1 stop7h 16m

Chicago Midway

Tue 11/25

6:05 am-5:41 pm

1 stop11h 36m

$221

MemphisChicago

MEM - ORD

MEMORD

Memphis

Wed 11/26

7:59 pm-12:10 am

1 stop28h 11m

Chicago O'Hare Intl

Sun 11/30

7:57 pm-7:04 pm

2 stops23h 07m

$230

MemphisChicago

MEM - ORD

MEMORD

Memphis

Wed 12/3

10:07 am-10:50 pm

2 stops12h 43m

Chicago O'Hare Intl

Wed 12/10

7:10 am-6:47 pm

2 stops11h 37m

$252

MemphisChicago

MEM - ORD

MEMORD

Memphis

Wed 12/3

10:07 am-10:50 pm

2 stops12h 43m

Chicago O'Hare Intl

Thu 12/4

7:10 am-6:47 pm

2 stops11h 37m

$253

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

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?

The month of September is, on average, the cheapest month to fly to Chicago from Mississippi, with most prices found around $301. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Mississippi to Chicago during August average around $342.

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

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $376. This is often the case because there is less demand to fly during this day of the week. When flying out on a Thursday, the most expensive travel day of the week, you can expect to see flight prices from Mississippi to Chicago for around $544.

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

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Mississippi to Chicago during this time can be as low as $362. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $597.

Can stopping save me money on Mississippi to Chicago flights?

You could potentially save up to 27% on your flight if you consider stops on a Mississippi to Chicago flight.

Cheap Mississippi to Chicago flight deals and tips

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

Fastest flight time

1h 35m

Direct flights

Every day

Airports in Chicago

2 airports
The fastest flight from Mississippi to Chicago takes 1h 35m
Direct flights go from Mississippi to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

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

    Prices for flights from Mississippi to Chicago are refreshed on a daily basis.

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

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

    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.

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

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Mississippi to Chicago

Compare and see reviews for airlines that fly from Mississippi to Chicago with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $116Free CancellationRating
7.9
8,004 reviews
Search Delta flights
SouthwestPriceFrom $234Free CancellationRating
8.0
4,240 reviews
Search Southwest flights
American AirlinesPriceFrom $248Free CancellationRating
7.2
11,042 reviews
Search American Airlines 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?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Mississippi to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

Flights from Mississippi 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 Mississippi to Chicago?

Once all potential Mississippi to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Mississippi and alert you when they change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport