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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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 6, 2025.

This Delta deal was found by Cheapflights users on 11/4. 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.
Wed 12/107:17 pmMOB - MDW
1 stop4h 30mDelta
Sat 12/136:00 amMDW - MOB
1 stop6h 40mDelta
Deal found 11/4$211
This Delta deal was found by Cheapflights users on 11/4. 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.
Tue 12/99:12 amMOB - ORD
1 stop6h 08mDelta
Sat 12/135:30 amORD - MOB
1 stop7h 10mDelta
Deal found 11/4$211
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Sun 11/237:11 pmMEM - ORD
1 stop18h 12mMultiple Airlines
Mon 12/16:15 pmORD - MEM
1 stop14h 47mMultiple Airlines
Deal found 11/6$211
This Delta deal was found by Cheapflights users on 11/6. 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.
Tue 12/96:30 amMEM - MDW
1 stop6h 04mDelta
Wed 12/106:00 amMDW - MEM
1 stop5h 42mDelta
Deal found 11/6$211
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Wed 11/267:59 pmMEM - ORD
1 stop28h 11mMultiple Airlines
Wed 12/32:28 pmORD - MEM
1 stop28h 03mMultiple Airlines
Deal found 11/6$212
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/57:42 pmMEM - ORD
1 stop17h 34mMultiple Airlines
Sun 12/72:36 pmORD - MEM
2 stops24h 57mMultiple Airlines
Deal found 11/4$214
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Wed 11/267:59 pmMEM - ORD
1 stop28h 11mFrontier
Thu 12/47:00 amORD - MEM
1 stop12h 12mFrontier
Deal found 11/6$216
This American Airlines deal was found by Cheapflights users on 11/5. 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 12/95:15 amMEM - ORD
1 stop8h 19mAmerican Airlines
Wed 12/101:32 pmORD - MEM
Nonstop1h 53mAmerican Airlines
Deal found 11/5$217
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Wed 11/267:59 pmMEM - ORD
1 stop28h 11mMultiple Airlines
Mon 12/16:15 pmORD - MEM
1 stop14h 47mMultiple Airlines
Deal found 11/6$218
This Kiwi.com deal was found by Cheapflights users on 11/4. 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
Thu 12/113:47 pmORD - MEM
2 stops28h 10mMultiple Airlines
Deal found 11/4$219
This Southwest deal was found by Cheapflights users on 11/4. 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 12/81:25 pmMEM - MDW
1 stop5h 55mSouthwest
Wed 12/248:15 amMDW - MEM
Nonstop1h 45mSouthwest
Deal found 11/4$220
This American Airlines deal was found by Cheapflights users on 11/4. 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 11/265:03 pmMEM - ORD
1 stop5h 53mAmerican Airlines
Wed 12/38:26 amORD - MEM
Nonstop1h 55mAmerican Airlines
Deal found 11/4$221

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 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$208
(United Airlines)

One-way from

$55
(Priceline)

Popular in

January

Cheapest in

September

Average price

$435
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. 6% potential increase in price ($29 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 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 6, 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

Tue 12/9

7:17 pm-11:47 pm

1 stop4h 30m

Chicago Midway

Sat 12/13

6:00 am-12:40 pm

1 stop6h 40m

$211

MobileChicago

MOB - MDW

MOBMDW

Mobile

Wed 12/10

7:17 pm-11:47 pm

1 stop4h 30m

Chicago Midway

Sat 12/13

6:00 am-12:40 pm

1 stop6h 40m

$211

MobileChicago

MOB - ORD

MOBORD

Mobile

Wed 4/15

7:15 pm-11:55 pm

1 stop4h 40m

Chicago O'Hare Intl

Sat 4/18

6:00 am-11:29 am

1 stop5h 29m

$211

MemphisChicago

MEM - ORD

MEMORD

Memphis

Mon 12/8

4:28 pm-12:12 am

1 stop7h 44m

Chicago O'Hare Intl

Wed 12/24

12:39 pm-7:07 pm

2 stops30h 28m

$219

MemphisChicago

MEM - ORD

MEMORD

Memphis

Thu 12/11

6:50 pm-11:46 pm

1 stop4h 56m

Chicago O'Hare Intl

Sun 12/14

10:04 pm-11:59 pm

Nonstop1h 55m

$228

MobileChicago

MOB - ORD

MOBORD

Mobile

Wed 12/3

2:55 pm-10:18 pm

1 stop7h 23m

Chicago O'Hare Intl

Wed 12/10

5:00 am-10:24 am

1 stop5h 24m

$230

MobileChicago

MOB - MDW

MOBMDW

Mobile

Wed 12/3

7:17 pm-11:47 pm

1 stop4h 30m

Chicago Midway

Wed 12/10

12:50 pm-6:32 pm

1 stop5h 42m

$230

MobileChicago

MOB - MDW

MOBMDW

Mobile

Mon 12/8

7:17 pm-11:47 pm

1 stop4h 30m

Chicago Midway

Sat 12/13

6:00 am-12:40 pm

1 stop6h 40m

$230

MobileChicago

MOB - MDW

MOBMDW

Mobile

Wed 12/10

7:17 pm-11:47 pm

1 stop4h 30m

Chicago Midway

Sun 12/14

6:00 am-12:43 pm

1 stop6h 43m

$230

MobileChicago

MOB - MDW

MOBMDW

Mobile

Fri 12/5

7:17 pm-11:47 pm

1 stop4h 30m

Chicago Midway

Sat 12/13

6:00 am-12:40 pm

1 stop6h 40m

$230

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

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 December is currently the most expensive (average of $339). 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 6, 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 4h 30m. Fly via Delta, American Airlines, or Frontier to get the fastest option. Airlines will cover a distance of 767 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 Frontier. According to our data, you can fly for as low as $78. Users have also found prices from $96 and $106 on United Airlines 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, Baton Rouge Ryan - Chicago O'Hare Intl and Memphis - Chicago Midway.

  • 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 December is currently the most expensive (average of $339). 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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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 6, 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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