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$64+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JAN
nov. 22 — nov. 291
sáb. 11/22
sáb. 11/29
1 adult, Economy
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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 octubre 23, 2025.

This American Airlines deal was found by Cheapflights users on 10/22. 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.
mar. 11/255:18 amORD - MEM
1 stop7h 11mAmerican Airlines
mar. 12/96:46 amMEM - ORD
Nonstop2h 03mAmerican Airlines
Deal found 10/22$212
This Southwest deal was found by Cheapflights users on 10/21. 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.
mar. 12/98:35 amMDW - MEM
2 stops8h 40mSouthwest
jue. 12/116:00 amMEM - MDW
2 stops8h 55mSouthwest
Deal found 10/21$215
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
lun. 11/310:43 pmORD - MEM
1 stop21h 55mMultiple Airlines
mar. 11/119:33 pmMEM - ORD
1 stop31h 59mMultiple Airlines
Deal found 10/20$218
This American Airlines deal was found by Cheapflights users on 10/22. 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.
jue. 12/48:26 amORD - MEM
Nonstop1h 55mAmerican Airlines
dom. 12/77:11 pmMEM - ORD
1 stop5h 39mAmerican Airlines
Deal found 10/22$219
This American Airlines deal was found by Cheapflights users on 10/20. 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.
vie. 12/53:44 pmORD - MEM
1 stop5h 11mAmerican Airlines
vie. 12/127:27 pmMEM - ORD
Nonstop2h 02mAmerican Airlines
Deal found 10/20$220
This Kiwi.com deal was found by Cheapflights users on 10/22. 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.
mié. 11/510:52 amORD - MEM
1 stop20h 40mMultiple Airlines
mar. 11/119:33 pmMEM - ORD
1 stop31h 59mMultiple Airlines
Deal found 10/22$221
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
mar. 12/98:00 amORD - MEM
2 stops9h 16mMultiple Airlines
jue. 12/116:21 pmMEM - ORD
1 stop19h 55mMultiple Airlines
Deal found 10/21$223
This Delta deal was found by Cheapflights users on 10/22. 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.
mar. 11/255:23 amORD - MEM
1 stop4h 01mDelta
mar. 12/95:55 amMEM - ORD
1 stop5h 45mDelta
Deal found 10/22$227
This Southwest deal was found by Cheapflights users on 10/21. 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.
mar. 11/188:10 amMDW - MEM
Nonstop1h 45mSouthwest
mié. 11/193:00 pmMEM - MDW
Nonstop1h 35mSouthwest
Deal found 10/21$231
This American Airlines deal was found by Cheapflights users on 10/22. 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.
mar. 11/188:20 amORD - MEM
Nonstop1h 53mAmerican Airlines
mar. 11/253:41 pmMEM - ORD
Nonstop2h 05mAmerican Airlines
Deal found 10/22$231
This Orbitz deal was found by Cheapflights users on 10/21. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/236:50 amORD - MEM
1 stop12h 33mMultiple Airlines
jue. 10/307:00 amMEM - ORD
1 stop10h 49mMultiple Airlines
Deal found 10/21$232
This American Airlines deal was found by Cheapflights users on 10/21. 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.
sáb. 11/222:03 pmORD - MEM
1 stop6h 08mAmerican Airlines
lun. 11/246:35 pmMEM - ORD
Nonstop2h 09mAmerican Airlines
Deal found 10/21$236

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 octubre 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$212
(American Airlines)

One-way from

$64
(United Airlines)

Popular in

November

Cheapest in

June

Average price

$482
Provider with most accurate pricing for Chicago (CHI)-Jackson-Evers Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Jackson-Evers Intl flights.
Search Deals
From Chicago (CHI) to Mississippi
Search Deals
One-way flight from Chicago (CHI) to Mississippi
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($70 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 octubre 23, 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

MDW - MEM

MDWMEM

Chicago Midway

mar. 12/9

8:35 am-5:15 pm

2 stops8h 40m

Memphis

jue. 12/11

6:00 am-2:55 pm

2 stops8h 55m

$215

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

dom. 2/15

12:20 pm-9:05 pm

2 stops8h 45m

Memphis

mié. 2/18

3:05 pm-4:45 pm

Nonstop1h 40m

$224

ChicagoMemphis

ORD - MEM

ORDMEM

Chicago O'Hare Intl

mar. 11/25

5:23 am-9:24 am

1 stop4h 01m

Memphis

mar. 12/9

5:55 am-11:40 am

1 stop5h 45m

$227

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

dom. 2/15

7:55 am-9:40 am

Nonstop1h 45m

Memphis

jue. 2/19

12:15 pm-10:20 pm

1 stop10h 05m

$228

ChicagoMemphis

ORD - MEM

ORDMEM

Chicago O'Hare Intl

mar. 11/18

8:20 am-10:13 am

Nonstop1h 53m

Memphis

mar. 11/25

3:41 pm-5:46 pm

Nonstop2h 05m

$231

ChicagoMemphis

ORD - MEM

ORDMEM

Chicago O'Hare Intl

mié. 11/26

3:43 pm-10:30 am

1 stop18h 47m

Memphis

mar. 12/2

10:07 am-11:06 pm

1 stop12h 59m

$238

ChicagoMemphis

ORD - MEM

ORDMEM

Chicago O'Hare Intl

sáb. 1/3

6:15 am-2:16 pm

1 stop8h 01m

Memphis

mar. 1/13

5:45 pm-7:56 pm

Nonstop2h 11m

$239

ChicagoMemphis

ORD - MEM

ORDMEM

Chicago O'Hare Intl

mié. 11/5

12:37 pm-7:32 am

2 stops18h 55m

Memphis

vie. 11/7

6:46 pm-11:06 pm

1 stop28h 20m

$241

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

mar. 11/18

8:50 am-2:10 pm

1 stop5h 20m

Memphis

mié. 11/19

7:30 am-9:05 am

Nonstop1h 35m

$241

ChicagoMemphis

MDW - MEM

MDWMEM

Chicago Midway

mié. 11/5

2:06 pm-7:32 am

2 stops17h 26m

Memphis

dom. 11/9

2:30 pm-3:22 pm

1 stop24h 52m

$242

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/22

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, April is the cheapest month in which you can book a flight from Chicago to Mississippi (average of $164). Flying from Chicago to Mississippi in January is currently the most expensive (average of $328). 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 octubre 23, 2025.

One of the essential ways to save on airfare from Chicago to Mississippi is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 15% on airfare.

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 octubre 23, 2025.
See what other customers who have flown with Southwest, Delta, and United 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
4,236 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,236 reviews
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,982 reviews
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,995 reviews
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,032 reviews
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Chicago to Mississippi?

    Airlines like Southwest, Delta, and American Airlines fly from Chicago to Mississippi in about 1h 53m. The time it takes to get you to your destination can typically vary by up to 6h 47m. Chicago and Mississippi are separated by a distance of 492 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $64. Users have also found prices from $73 and $120 on Southwest and Delta, 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 - Mobile 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, April is the cheapest month in which you can book a flight from Chicago to Mississippi (average of $164). Flying from Chicago to Mississippi in January is currently the most expensive (average of $328). 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 4 airlines flying from Chicago to Mississippi

Discover the top 4 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 octubre 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$236Average$356FlexibilityNo cancel feeOn-time71%
DeltaCheapest$248Average$440FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$316Average$466FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$356Average$449FlexibilityNo cancel feeOn-time69%

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