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$75+ 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 9/22. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
ago. 19 — ago. 261
mar. 8/19
mar. 8/26
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 agosto 14, 2025.

Round-trip from

$185
(FlightHub)

One-way from

$75
(Priceline)

Popular in

January

Cheapest in

May

Average price

$416
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. 4% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in August 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 agosto 14, 2025.

This FlightHub deal was found by Cheapflights users on 8/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/67:00 amMEM - ORD
1 stop9h 12mMultiple Airlines
dom. 9/76:00 amORD - MEM
1 stop13h 19mMultiple Airlines
Deal found 8/14$185
This Southwest deal was found by Cheapflights users on 8/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/1010:55 amMEM - MDW
2 stops6h 50mSouthwest
mié. 9/1712:50 pmMDW - MEM
2 stops7h 25mSouthwest
Deal found 8/14$185
This Southwest deal was found by Cheapflights users on 8/13. 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.
lun. 9/81:55 pmMEM - ORD
1 stop7h 35mSouthwest
mié. 9/103:10 pmORD - MEM
1 stop4h 30mSouthwest
Deal found 8/13$186
This Delta deal was found by Cheapflights users on 8/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/62:03 pmMEM - ORD
1 stop6h 20mDelta
mié. 9/105:45 amORD - MEM
1 stop5h 56mDelta
Deal found 8/14$187
This Delta deal was found by Cheapflights users on 8/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/275:20 amMEM - MDW
1 stop4h 28mDelta
mié. 10/19:35 amMDW - MEM
1 stop3h 47mDelta
Deal found 8/14$187
This United Airlines deal was found by Cheapflights users on 8/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/57:30 amMEM - ORD
Nonstop2h 01mUnited Airlines
lun. 9/87:45 pmORD - MEM
Nonstop1h 58mUnited Airlines
Deal found 8/14$188
This Southwest deal was found by Cheapflights users on 8/12. 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.
vie. 9/196:40 amMEM - MDW
Nonstop1h 40mSouthwest
lun. 9/228:45 pmMDW - MEM
Nonstop1h 40mSouthwest
Deal found 8/12$188
This Southwest deal was found by Cheapflights users on 8/13. 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.
mié. 9/1010:55 amMEM - ORD
1 stop12h 10mSouthwest
mar. 9/167:30 amORD - MEM
2 stops12h 10mSouthwest
Deal found 8/13$191
This Southwest deal was found by Cheapflights users on 8/12. 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.
mié. 9/33:30 pmMEM - MDW
2 stops6h 25mSouthwest
jue. 9/45:45 amMDW - MEM
1 stop5h 50mSouthwest
Deal found 8/12$191
This Southwest deal was found by Cheapflights users on 8/12. 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.
lun. 9/812:20 pmMEM - MDW
2 stops8h 30mSouthwest
jue. 9/118:45 pmMDW - MEM
Nonstop1h 40mSouthwest
Deal found 8/12$192
This FlightHub deal was found by Cheapflights users on 8/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/27:00 amMEM - ORD
1 stop11h 50mSpirit Airlines
dom. 10/56:00 amORD - MEM
1 stop9h 12mSpirit Airlines
Deal found 8/14$193
This Southwest deal was found by Cheapflights users on 8/12. 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.
sáb. 9/1311:50 amMEM - MDW
1 stop11h 00mSouthwest
lun. 9/158:45 pmMDW - MEM
Nonstop1h 40mSouthwest
Deal found 8/12$193

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 agosto 14, 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

sáb. 9/6

7:00 am-4:12 pm

1 stop9h 12m

Chicago O'Hare Intl

dom. 9/7

6:00 am-7:19 pm

1 stop13h 19m

$185

MemphisChicago

MEM - MDW

MEMMDW

Memphis

mié. 9/10

10:55 am-5:45 pm

2 stops6h 50m

Chicago Midway

mié. 9/17

11:45 am-7:40 pm

2 stops7h 55m

$185

MemphisChicago

MEM - ORD

MEMORD

Memphis

mar. 9/9

10:55 am-4:45 pm

1 stop5h 50m

Chicago O'Hare Intl

mié. 9/10

7:30 am-8:15 pm

2 stops12h 45m

$186

MemphisChicago

MEM - ORD

MEMORD

Memphis

lun. 9/22

1:55 pm-9:30 pm

1 stop7h 35m

Chicago O'Hare Intl

mar. 9/30

3:10 pm-7:40 pm

1 stop4h 30m

$186

MemphisChicago

MEM - ORD

MEMORD

Memphis

lun. 9/8

1:55 pm-9:30 pm

1 stop7h 35m

Chicago O'Hare Intl

mié. 9/10

3:10 pm-7:40 pm

1 stop4h 30m

$186

MemphisChicago

MEM - ORD

MEMORD

Memphis

mié. 9/3

10:14 am-4:13 pm

1 stop5h 59m

Chicago O'Hare Intl

sáb. 9/6

5:45 am-11:41 am

1 stop5h 56m

$187

MemphisChicago

MEM - ORD

MEMORD

Memphis

mié. 9/17

10:30 am-4:20 pm

1 stop5h 50m

Chicago O'Hare Intl

lun. 9/22

5:00 pm-8:57 pm

1 stop3h 57m

$187

MemphisChicago

MEM - ORD

MEMORD

Memphis

mié. 10/15

7:05 am-12:16 pm

1 stop5h 11m

Chicago O'Hare Intl

sáb. 10/18

6:08 am-11:20 am

1 stop5h 12m

$187

MemphisChicago

MEM - ORD

MEMORD

Memphis

lun. 9/22

7:01 pm-11:54 pm

1 stop4h 53m

Chicago O'Hare Intl

mar. 9/30

9:10 am-1:22 pm

1 stop4h 12m

$187

MemphisChicago

MEM - ORD

MEMORD

Memphis

mié. 2/4

7:20 pm-11:54 pm

1 stop4h 34m

Chicago O'Hare Intl

sáb. 2/7

6:00 am-11:23 am

1 stop5h 23m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

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 agosto 14, 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.

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.

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

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $75. Users have also found prices from $78 and $78 on United Airlines and Southwest, 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

Browse thousands of different options on Cheapflights for your next trip

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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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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 agosto 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$495FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$234Average$392FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$248Average$431FlexibilityNo cancel feeOn-time71%

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