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$61+ Cheap flights from Chicago (CHI) to Mississippi

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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JAN
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Chicago to Mississippi

Keep the following information in mind while searching for Chicago to Mississippi flight deals. Data was last updated August 14, 2025.

Round-trip from

$173
(Mytrip)

One-way from

$61
(FlightHub)

Popular in

April

Cheapest in

October

Average price

$392
From Chicago (CHI) to Mississippi
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One-way flight from Chicago (CHI) to Mississippi
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($49 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 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 Chicago to Mississippi

Cheapest flights from Chicago to Mississippi
Explore the most affordable flight options available from Chicago to Mississippi. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/410:42 amORD - MEM
1 stop7h 25mFrontier
Sun 9/78:04 pmMEM - ORD
1 stop27h 55mFrontier
Deal found 8/13$173
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.
Mon 9/88:45 pmMDW - MEM
Nonstop1h 40mSouthwest
Tue 9/98:30 amMEM - MDW
1 stop6h 00mSouthwest
Deal found 8/14$176
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/308:58 amORD - MEM
Nonstop2h 00mUnited Airlines
Tue 9/27:30 amMEM - ORD
Nonstop2h 01mUnited Airlines
Deal found 8/12$176
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.
Thu 9/47:55 amMDW - MEM
Nonstop1h 35mSouthwest
Mon 9/86:40 amMEM - MDW
Nonstop1h 40mSouthwest
Deal found 8/14$177
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/412:50 pmORD - MEM
Nonstop2h 00mUnited Airlines
Sat 9/67:30 amMEM - ORD
Nonstop2h 01mUnited Airlines
Deal found 8/13$177
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/44:55 pmORD - MEM
Nonstop1h 53mAmerican Airlines
Mon 9/85:18 pmMEM - ORD
Nonstop2h 08mAmerican Airlines
Deal found 8/13$178
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.
Tue 9/166:25 amMDW - MEM
1 stop6h 40mSouthwest
Wed 9/173:30 pmMEM - MDW
2 stops6h 25mSouthwest
Deal found 8/14$180
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1111:49 amORD - MEM
Nonstop1h 50mAmerican Airlines
Thu 9/185:18 pmMEM - ORD
Nonstop2h 08mAmerican Airlines
Deal found 8/12$181
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.
Wed 9/33:10 pmORD - MEM
1 stop4h 30mSouthwest
Mon 9/81:55 pmMEM - ORD
1 stop7h 35mSouthwest
Deal found 8/12$186
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/318:02 amORD - MEM
Nonstop1h 47mAmerican Airlines
Mon 11/36:46 amMEM - ORD
Nonstop2h 01mAmerican Airlines
Deal found 8/12$187
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.
Thu 9/118:45 pmMDW - MEM
Nonstop1h 40mSouthwest
Thu 9/186:10 pmMEM - MDW
Nonstop1h 35mSouthwest
Deal found 8/14$188
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/257:50 pmORD - MEM
Nonstop1h 58mUnited Airlines
Sun 9/287:30 amMEM - ORD
Nonstop2h 01mUnited Airlines
Deal found 8/12$188

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Mississippi 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 August 14, 2025.
Use the filters below to find and compare flights from Chicago to Mississippi that are best for you.

Fly from

Chicago

Fly to

Mississippi

Route

Depart

Return

Price

ChicagoMemphis

ORD - MEM

ORDMEM

Chicago O'Hare Intl

Thu 9/4

10:42 am-6:07 pm

1 stop7h 25m

Memphis

Sun 9/7

8:04 pm-11:59 pm

1 stop27h 55m

$173

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

Wed 9/3

8:25 pm-10:05 pm

Nonstop1h 40m

Memphis

Mon 9/8

1:55 pm-8:50 pm

1 stop6h 55m

$176

ChicagoMemphis

ORD - MEM

ORDMEM

Chicago O'Hare Intl

Sat 8/30

8:58 am-10:58 am

Nonstop2h 00m

Memphis

Tue 9/2

7:30 am-9:31 am

Nonstop2h 01m

$176

ChicagoMemphis

ORD - MEM

ORDMEM

Chicago O'Hare Intl

Sat 8/30

12:05 pm-1:56 pm

Nonstop1h 51m

Memphis

Tue 9/2

2:26 pm-4:25 pm

Nonstop1h 59m

$176

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

Wed 9/10

6:25 am-1:05 pm

1 stop6h 40m

Memphis

Thu 9/11

6:10 pm-7:45 pm

Nonstop1h 35m

$176

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

Sat 9/20

8:30 am-10:10 am

Nonstop1h 40m

Memphis

Tue 9/23

3:30 pm-7:45 pm

1 stop4h 15m

$176

ChicagoMemphis

ORD - MEM

ORDMEM

Chicago O'Hare Intl

Wed 9/10

9:10 am-1:23 pm

1 stop4h 13m

Memphis

Wed 9/17

6:30 am-10:19 am

1 stop3h 49m

$177

ChicagoMemphis

ORD - MEM

ORDMEM

Chicago O'Hare Intl

Thu 9/4

12:50 pm-2:50 pm

Nonstop2h 00m

Memphis

Sat 9/6

7:30 am-9:31 am

Nonstop2h 01m

$177

ChicagoMemphis

ORD - MEM

ORDMEM

Chicago O'Hare Intl

Thu 9/4

1:10 pm-2:59 pm

Nonstop1h 49m

Memphis

Mon 9/8

2:11 pm-4:10 pm

Nonstop1h 59m

$177

ChicagoMemphis

ORD - MEM

ORDMEM

Chicago O'Hare Intl

Thu 9/11

11:49 am-1:39 pm

Nonstop1h 50m

Memphis

Thu 9/18

5:18 pm-7:26 pm

Nonstop2h 08m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

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

Have a flexible travel schedule? Discover the best time to fly to Mississippi from Chicago 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 Chicago to Mississippi

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Mississippi (average of $371). Flying from Chicago to Mississippi in March is currently the most expensive (average of $448). 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 CHI to MS?

Find hourly flight availability from Chicago to Mississippi. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

When flying from Chicago to Mississippi, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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

Reviews of airlines servicing Mississippi

Get insights into the airlines that provide service to Mississippi. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Mississippi. Reviews last updated August 14, 2025.
See what other customers who have flown with Southwest, Delta, and American Airlines from Chicago to Mississippi have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Mississippi. 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 Chicago to Mississippi one-way?

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $61. Users have also found prices from $75 and $78 on Frontier and Southwest, respectively.

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

    When deciding which route to take from Chicago to Mississippi consider Chicago O'Hare Intl - Memphis, Chicago Midway - Memphis or Chicago O'Hare Intl - Jackson-Evers Intl as they are the most popular.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Mississippi 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 Chicago to Mississippi?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Mississippi (average of $371). Flying from Chicago to Mississippi in March is currently the most expensive (average of $448). 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

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Alternative routes for Chicago to Mississippi

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

Discover the top 3 airlines that operate flights from Chicago to Mississippi. 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$429FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$248Average$363FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$316Average$464FlexibilityNo cancel feeOn-time63%

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