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$70+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
ene. 11 — ene. 181
dom. 1/11
dom. 1/18
1 adult, Economy
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Cheap 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 diciembre 12, 2025.

This Southwest deal was found by Cheapflights users on 12/10. 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. 12/317:30 amMEM - MDW
Nonstop1h 35mSouthwest
jue. 1/19:20 amMDW - MEM
1 stop5h 30mSouthwest
Deal found 12/10$199
This Delta deal was found by Cheapflights users on 12/9. 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.
jue. 12/255:01 pmMEM - ORD
1 stop7h 01mDelta
jue. 1/16:35 amORD - MEM
1 stop4h 58mDelta
Deal found 12/9$209
This American Airlines deal was found by Cheapflights users on 12/10. 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.
mié. 12/315:28 pmMEM - ORD
Nonstop2h 05mAmerican Airlines
mar. 1/65:05 amORD - MEM
1 stop5h 56mAmerican Airlines
Deal found 12/10$220
This American Airlines deal was found by Cheapflights users on 12/9. 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.
mié. 12/246:15 amMEM - ORD
Nonstop2h 08mAmerican Airlines
jue. 1/14:07 pmORD - MEM
1 stop6h 19mAmerican Airlines
Deal found 12/9$229
This United Airlines deal was found by Cheapflights users on 12/9. 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.
mié. 12/247:30 amMEM - ORD
Nonstop2h 03mUnited Airlines
mié. 12/317:35 amORD - MEM
Nonstop2h 06mUnited Airlines
Deal found 12/9$249
This Kiwi.com deal was found by Cheapflights users on 12/9. 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. 12/238:47 pmMEM - ORD
2 stops42h 15mMultiple Airlines
dom. 1/410:49 pmORD - MEM
1 stop18h 00mMultiple Airlines
Deal found 12/9$255
This Kiwi.com deal was found by Cheapflights users on 12/9. 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. 12/248:13 pmMEM - ORD
2 stops18h 49mMultiple Airlines
dom. 1/410:49 pmORD - MEM
1 stop18h 00mMultiple Airlines
Deal found 12/9$257
This American Airlines deal was found by Cheapflights users on 12/10. 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.
mié. 12/246:15 amMEM - ORD
Nonstop2h 08mAmerican Airlines
mar. 12/301:27 pmORD - MEM
Nonstop1h 52mAmerican Airlines
Deal found 12/10$260
This Southwest deal was found by Cheapflights users on 12/10. 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. 12/243:00 pmMEM - MDW
Nonstop1h 35mSouthwest
mar. 12/3010:20 pmMDW - MEM
Nonstop1h 45mSouthwest
Deal found 12/10$260
This Delta deal was found by Cheapflights users on 12/9. 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.
mié. 12/245:01 pmMEM - ORD
1 stop7h 01mDelta
jue. 1/16:35 amORD - MEM
1 stop4h 58mDelta
Deal found 12/9$264
This Kiwi.com deal was found by Cheapflights users on 12/9. 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. 12/238:47 pmMEM - ORD
2 stops42h 15mMultiple Airlines
jue. 1/16:00 amORD - MEM
1 stop9h 08mMultiple Airlines
Deal found 12/9$266
This Kiwi.com deal was found by Cheapflights users on 12/9. 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. 12/248:13 pmMEM - ORD
2 stops18h 49mMultiple Airlines
jue. 1/16:00 amORD - MEM
1 stop9h 08mMultiple Airlines
Deal found 12/9$269

Find flight deals from Mississippi to Chicago

Keep the following information in mind while searching for Mississippi to Chicago flight deals. Data was last updated diciembre 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$195
(Kiwi.com)

One-way from

$70
(Frontier)

Popular in

January

Cheapest in

September

Average price

$321
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. 4% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 diciembre 12, 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

jue. 1/15

5:45 pm-7:56 pm

Nonstop2h 11m

Chicago O'Hare Intl

dom. 1/18

9:11 pm-11:07 pm

Nonstop1h 56m

$215

MemphisChicago

MEM - MDW

MEMMDW

Memphis

jue. 1/15

7:05 am-8:50 am

Nonstop1h 45m

Chicago Midway

dom. 1/18

8:10 am-9:55 am

Nonstop1h 45m

$215

MemphisChicago

MEM - MDW

MEMMDW

Memphis

mié. 12/31

6:45 am-2:30 pm

1 stop7h 45m

Chicago Midway

jue. 1/1

10:50 am-4:05 pm

1 stop5h 15m

$239

MobileChicago

MOB - ORD

MOBORD

Mobile

jue. 2/12

6:40 pm-11:53 pm

1 stop5h 13m

Chicago O'Hare Intl

mar. 2/17

4:05 pm-11:11 pm

1 stop7h 06m

$250

MemphisChicago

MEM - ORD

MEMORD

Memphis

jue. 1/1

7:30 am-9:33 am

Nonstop2h 03m

Chicago O'Hare Intl

dom. 1/4

7:35 am-9:41 am

Nonstop2h 06m

$260

MemphisChicago

MEM - MDW

MEMMDW

Memphis

vie. 1/16

3:30 pm-5:05 pm

Nonstop1h 35m

Chicago Midway

dom. 1/18

8:10 am-9:55 am

Nonstop1h 45m

$260

MemphisChicago

MEM - ORD

MEMORD

Memphis

lun. 1/26

4:12 pm-9:04 pm

1 stop4h 52m

Chicago O'Hare Intl

jue. 1/29

9:55 am-3:02 pm

1 stop5h 07m

$261

MemphisChicago

MEM - ORD

MEMORD

Memphis

lun. 1/19

10:32 am-4:38 pm

1 stop6h 06m

Chicago O'Hare Intl

jue. 1/22

11:17 am-4:16 pm

1 stop4h 59m

$261

MemphisChicago

MEM - ORD

MEMORD

Memphis

vie. 2/13

7:30 am-9:25 am

Nonstop1h 55m

Chicago O'Hare Intl

mar. 2/17

7:59 pm-9:59 pm

Nonstop2h 00m

$264

MemphisChicago

MEM - ORD

MEMORD

Memphis

mié. 12/24

5:01 pm-12:02 am

1 stop7h 01m

Chicago O'Hare Intl

mié. 12/31

6:35 am-11:33 am

1 stop4h 58m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

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 $331). 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 diciembre 12, 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.

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 45m. Fly via American Airlines, Southwest, or United Airlines to get the fastest option. Airlines will cover a distance of 481 mi. All flights are typically nonstop.

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

    For one-way options, check prices for Turkish Airlines. According to our data, you can fly for as low as $493. Users have also found prices from $506 and $586 on LOT and Lufthansa, 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 $331). 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
Merrillville
Hammond
Porter
Benton Harbor

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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 diciembre 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$196Average$477FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$234Average$392FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$248Average$406FlexibilityNo cancel feeOn-time71%

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