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$90+ Cheap flights from Mississippi to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/26. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Mississippi to Chicago

Keep the following information in mind while searching for Mississippi to Chicago flight deals. Data was last updated September 17, 2025.

Round-trip from

$191
(Kiwi.com)

One-way from

$90
(Kiwi.com)

Popular in

January

Cheapest in

September

Average price

$301
From Mississippi to Chicago (CHI)
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One-way flight from Mississippi to Chicago (CHI)
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Highest demand for flights based on searches. 7% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Mississippi to Chicago

Cheapest flights from Mississippi to Chicago
Explore the most affordable flight options available from Mississippi to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/178:12 pmMEM - ORD
1 stop27h 41mMultiple Airlines
Sun 10/265:50 amORD - MEM
1 stop14h 00mMultiple Airlines
Deal found 9/14$191
This Frontier deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/248:12 pmMEM - ORD
2 stops15h 23mFrontier
Sun 10/2610:51 amORD - MEM
1 stop8h 34mFrontier
Deal found 9/15$193
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/238:10 pmMEM - ORD
1 stop13h 26mMultiple Airlines
Sun 10/265:50 amORD - MEM
1 stop12h 41mMultiple Airlines
Deal found 9/15$194
This Frontier deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/38:10 pmMEM - MDW
2 stops15h 28mFrontier
Thu 11/612:30 pmMDW - MEM
1 stop6h 52mFrontier
Deal found 9/15$194
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/48:00 pmMEM - ORD
1 stop22h 34mFrontier
Sun 12/77:39 pmORD - MEM
1 stop23h 26mFrontier
Deal found 9/15$195
This Mytrip deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/297:00 amMEM - ORD
1 stop9h 23mSpirit Airlines
Sat 11/15:28 pmORD - MEM
1 stop5h 40mSpirit Airlines
Deal found 9/15$196
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/72:48 pmMEM - ORD
Nonstop2h 08mUnited Airlines
Tue 10/147:50 pmORD - MEM
Nonstop1h 58mUnited Airlines
Deal found 9/15$197
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/213:20 pmMEM - MDW
Nonstop1h 35mSouthwest
Wed 10/227:45 amMDW - MEM
Nonstop1h 35mSouthwest
Deal found 9/16$197
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/145:30 pmMEM - ORD
Nonstop2h 07mAmerican Airlines
Tue 10/213:11 pmORD - MEM
Nonstop1h 49mAmerican Airlines
Deal found 9/15$198
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/248:12 pmMEM - ORD
1 stop27h 41mMultiple Airlines
Mon 10/278:15 amORD - MEM
1 stop14h 53mMultiple Airlines
Deal found 9/15$199
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/205:48 pmMEM - ORD
2 stops16h 20mMultiple Airlines
Thu 10/236:50 amORD - MEM
1 stop12h 33mMultiple Airlines
Deal found 9/15$202
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/248:12 pmMEM - ORD
1 stop27h 41mMultiple Airlines
Sun 10/266:00 amORD - MEM
1 stop17h 08mMultiple Airlines
Deal found 9/15$203

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated September 17, 2025.
Use the filters below to find and compare flights from Mississippi to Chicago that are best for you.

Fly from

Mississippi

Fly to

Chicago

Route

Depart

Return

Price

MemphisChicago

MEM - ORD

MEMORD

Memphis

Tue 10/7

2:48 pm-4:56 pm

Nonstop2h 08m

Chicago O'Hare Intl

Tue 10/14

7:50 pm-9:48 pm

Nonstop1h 58m

$197

MemphisChicago

MEM - ORD

MEMORD

Memphis

Tue 11/18

2:55 pm-4:59 pm

Nonstop2h 04m

Chicago O'Hare Intl

Wed 11/19

8:50 am-10:56 am

Nonstop2h 06m

$197

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Mon 10/27

6:55 am-8:35 am

Nonstop1h 40m

Chicago Midway

Wed 10/29

8:40 pm-10:15 pm

Nonstop1h 35m

$207

MemphisChicago

MEM - ORD

MEMORD

Memphis

Tue 10/21

7:30 am-9:31 am

Nonstop2h 01m

Chicago O'Hare Intl

Sat 10/25

7:50 pm-9:48 pm

Nonstop1h 58m

$207

MobileChicago

MOB - MDW

MOBMDW

Mobile

Sat 11/1

5:43 am-9:45 am

1 stop4h 02m

Chicago Midway

Sat 11/8

10:35 am-3:39 pm

1 stop5h 04m

$211

MobileChicago

MOB - ORD

MOBORD

Mobile

Tue 12/9

5:08 am-10:37 am

1 stop5h 29m

Chicago O'Hare Intl

Sat 12/13

3:14 pm-11:04 pm

1 stop7h 50m

$211

MobileChicago

MOB - ORD

MOBORD

Mobile

Sat 11/1

5:43 am-12:16 pm

1 stop6h 33m

Chicago O'Hare Intl

Sat 11/8

4:09 pm-10:48 pm

1 stop6h 39m

$211

MobileChicago

MOB - ORD

MOBORD

Mobile

Sat 10/18

1:17 pm-6:49 pm

1 stop5h 32m

Chicago O'Hare Intl

Sat 10/25

6:10 pm-10:48 pm

1 stop4h 38m

$211

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Fri 10/31

2:10 pm-3:50 pm

Nonstop1h 40m

Chicago Midway

Mon 11/3

8:40 pm-10:25 pm

Nonstop1h 45m

$217

MemphisChicago

MEM - ORD

MEMORD

Memphis

Tue 10/21

2:07 pm-8:23 pm

1 stop6h 16m

Chicago O'Hare Intl

Wed 10/22

5:20 am-11:32 am

1 stop6h 12m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 60 results
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Best time to book a flight from Mississippi to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Mississippi with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Mississippi to Chicago

What is the cheapest month to book a flight from Mississippi to Chicago?

Currently, August is the cheapest month in which you can book a flight from Mississippi to Chicago (average of $245). Flying from Mississippi to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MS to CHI?

Find hourly flight availability from Mississippi to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Mississippi to Chicago as you normally would.

How much does it cost to fly round-trip from Mississippi to Chicago?

Related info for your journey

Find useful and relevant information for your journey from Mississippi to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Mississippi to Chicago?

    There are many flights that can get you from Mississippi to Chicago in 1h 40m. Fly via United Airlines, Southwest, or Delta to get the fastest option. Airlines will cover a distance of 481 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Mississippi to Chicago one-way?

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $99. Users have also found prices from $99 and $100 on Southwest and American Airlines, respectively.

  • What are the most popular routes from Mississippi to Chicago?

    The most popular flight routes from Mississippi to Chicago are Memphis - Chicago O'Hare Intl, Memphis - Chicago Midway and Baton Rouge Ryan - Chicago O'Hare Intl.

  • Can I find deals for flights from Mississippi to Chicago that include hotel bookings?

    Yes. In addition to deals on Mississippi to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Mississippi to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Mississippi to Chicago.

  • Can I find deals for business class flights from Mississippi to Chicago?

    Yes. Cheapflights offers flight deals from Mississippi to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Mississippi to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Mississippi to Chicago (average of $245). Flying from Mississippi to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Mississippi to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Atlanta to Midway flights
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Top 3 airlines flying from Mississippi to Chicago

Discover the top 3 airlines that operate flights from Mississippi to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$473FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$234Average$392FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$248Average$405FlexibilityNo cancel feeOn-time71%

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