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$55+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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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 November 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/20. 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 12/127:42 pmMEM - ORD
1 stop17h 34mMultiple Airlines
Sun 12/148:45 amORD - MEM
1 stop9h 46mMultiple Airlines
Deal found 11/20$222
This American Airlines deal was found by Cheapflights users on 11/20. 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.
Wed 12/1010:29 amMEM - ORD
1 stop7h 33mAmerican Airlines
Wed 12/178:26 amORD - MEM
Nonstop1h 55mAmerican Airlines
Deal found 11/20$224
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 12/47:42 pmMEM - ORD
2 stops15h 26mMultiple Airlines
Sun 12/77:00 amORD - MEM
1 stop12h 12mMultiple Airlines
Deal found 11/18$226
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 12/55:48 pmMEM - ORD
2 stops41h 40mMultiple Airlines
Tue 12/165:00 amORD - MEM
1 stop7h 32mMultiple Airlines
Deal found 11/18$227
This Kiwi.com deal was found by Cheapflights users on 11/18. 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.
Tue 12/210:07 amMEM - ORD
1 stop12h 59mMultiple Airlines
Tue 12/95:00 amORD - MEM
1 stop7h 32mMultiple Airlines
Deal found 11/18$228
This American Airlines deal was found by Cheapflights users on 11/18. 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 12/910:51 amMEM - ORD
Nonstop1h 55mAmerican Airlines
Thu 12/116:35 pmORD - MEM
1 stop5h 29mAmerican Airlines
Deal found 11/18$229
This Southwest deal was found by Cheapflights users on 11/18. 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 12/93:30 pmMEM - MDW
1 stop4h 45mSouthwest
Thu 12/118:40 pmMDW - MEM
Nonstop1h 45mSouthwest
Deal found 11/18$229
This American Airlines deal was found by Cheapflights users on 11/19. 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.
Thu 12/255:13 amMOB - ORD
1 stop7h 27mAmerican Airlines
Mon 1/56:37 pmORD - MOB
1 stop5h 19mAmerican Airlines
Deal found 11/19$230
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 12/47:11 pmMEM - ORD
1 stop17h 28mMultiple Airlines
Sat 12/67:20 amORD - MEM
1 stop11h 27mMultiple Airlines
Deal found 11/18$230
This American Airlines deal was found by Cheapflights users on 11/19. 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.
Thu 11/275:15 amMEM - ORD
1 stop10h 04mAmerican Airlines
Fri 11/2810:29 amORD - MEM
1 stop7h 33mAmerican Airlines
Deal found 11/19$231
This Southwest deal was found by Cheapflights users on 11/18. 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.
Sat 12/137:15 amMEM - MDW
Nonstop1h 35mSouthwest
Tue 12/168:10 amMDW - MEM
Nonstop1h 45mSouthwest
Deal found 11/18$231
This American Airlines deal was found by Cheapflights users on 11/20. 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.
Thu 12/187:05 amMEM - ORD
1 stop7h 07mAmerican Airlines
Thu 12/255:21 amORD - MEM
1 stop11h 00mAmerican Airlines
Deal found 11/20$232

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 November 20, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$211
(Delta)

One-way from

$55
(Frontier)

Popular in

January

Cheapest in

September

Average price

$512
Provider with most accurate pricing for Jackson-Evers Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Jackson-Evers Intl-Chicago (CHI) flights.
Search Deals
From Mississippi to Chicago (CHI)
Search Deals
One-way flight from Mississippi to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 20, 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

MobileChicago

MOB - MDW

MOBMDW

Mobile

Sat 2/14

6:00 am-10:15 am

1 stop4h 15m

Chicago Midway

Tue 2/17

6:40 pm-11:00 pm

1 stop4h 20m

$211

MobileChicago

MOB - ORD

MOBORD

Mobile

Wed 1/28

5:40 am-11:55 am

1 stop6h 15m

Chicago O'Hare Intl

Sat 1/31

10:10 am-4:59 pm

1 stop6h 49m

$211

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Mon 12/15

7:30 am-9:05 am

Nonstop1h 35m

Chicago Midway

Wed 12/17

9:40 am-5:15 pm

1 stop7h 35m

$229

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Tue 12/9

3:30 pm-8:15 pm

1 stop4h 45m

Chicago Midway

Thu 12/11

8:40 pm-10:25 pm

Nonstop1h 45m

$229

MemphisChicago

MEM - ORD

MEMORD

Memphis

Tue 12/9

7:39 am-9:35 am

Nonstop1h 56m

Chicago O'Hare Intl

Sat 12/13

8:00 pm-9:59 pm

Nonstop1h 59m

$231

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Sat 12/13

7:15 am-8:50 am

Nonstop1h 35m

Chicago Midway

Tue 12/16

8:10 am-9:55 am

Nonstop1h 45m

$231

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Tue 1/20

3:05 pm-4:45 pm

Nonstop1h 40m

Chicago Midway

Thu 1/22

1:20 pm-8:05 pm

2 stops6h 45m

$234

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Sat 12/6

7:15 am-8:50 am

Nonstop1h 35m

Chicago Midway

Mon 12/15

8:40 pm-10:25 pm

Nonstop1h 45m

$236

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Sat 12/13

7:15 am-8:50 am

Nonstop1h 35m

Chicago Midway

Mon 12/15

8:40 pm-10:25 pm

Nonstop1h 45m

$236

MemphisChicago

MEM - ORD

MEMORD

Memphis

Tue 11/25

2:55 pm-4:59 pm

Nonstop2h 04m

Chicago O'Hare Intl

Fri 11/28

12:45 pm-2:45 pm

Nonstop2h 00m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

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 $196). Flying from Mississippi to Chicago in May is currently the most expensive (average of $334). 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 November 20, 2025.

One of the essential ways to save on airfare from Mississippi to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 28% on airfare.

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 35m. Fly via Delta, American Airlines, or Southwest 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 $125 on Southwest and Delta, 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 Jackson-Evers Intl - 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 $196). Flying from Mississippi to Chicago in May is currently the most expensive (average of $334). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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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Denver 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 November 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$460FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$234Average$406FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$248Average$407FlexibilityNo cancel feeOn-time71%

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