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$64+ 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 junio 12, 2025.

Round-trip from

$209
(Booking.com)

One-way from

$64
(United Airlines)

Popular in

January

Cheapest in

May

Average price

$392
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. 5% potential increase in price ($24 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 June 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 junio 12, 2025.

This Booking.com deal was found by Cheapflights users on 6/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/211:49 amMEM - ORD
1 stop8h 34mSpirit Airlines
mié. 7/910:00 amORD - MEM
1 stop6h 29mSpirit Airlines
Deal found 6/10$209
This American Airlines deal was found by Cheapflights users on 6/11. 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. 7/194:34 pmMOB - ORD
1 stop4h 57mAmerican Airlines
mié. 7/235:00 amORD - MOB
1 stop6h 53mAmerican Airlines
Deal found 6/11$211
This Southwest deal was found by Cheapflights users on 6/11. 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. 8/223:35 pmMEM - MDW
1 stop6h 25mSouthwest
dom. 8/248:10 amMDW - MEM
Nonstop1h 35mSouthwest
Deal found 6/11$211
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/297:30 amMEM - ORD
Nonstop2h 01mUnited Airlines
lun. 9/18:58 amORD - MEM
Nonstop2h 00mUnited Airlines
Deal found 6/10$214
This American Airlines deal was found by Cheapflights users on 6/10. 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. 7/25:05 pmMEM - ORD
Nonstop2h 19mAmerican Airlines
mié. 7/910:11 pmORD - MEM
Nonstop1h 56mAmerican Airlines
Deal found 6/10$216
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/3011:10 amMEM - ORD
1 stop5h 18mDelta
dom. 8/315:45 amORD - MEM
1 stop4h 40mDelta
Deal found 6/10$218
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/16:30 amMEM - MDW
1 stop5h 59mDelta
jue. 7/316:00 amMDW - MEM
1 stop5h 38mDelta
Deal found 6/12$219
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/3012:30 pmMOB - ORD
1 stop6h 49mDelta
dom. 8/315:45 amORD - MOB
1 stop5h 48mDelta
Deal found 6/10$221
This Mytrip deal was found by Cheapflights users on 6/11. 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.
lun. 7/2110:06 pmMEM - ORD
1 stop16h 07mMultiple Airlines
mar. 7/224:36 pmORD - MEM
1 stop23h 53mMultiple Airlines
Deal found 6/11$232
This Southwest deal was found by Cheapflights users on 6/10. 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.
sáb. 12/65:35 amMEM - ORD
1 stop7h 25mSouthwest
vie. 12/121:45 pmORD - MEM
2 stops8h 10mSouthwest
Deal found 6/10$239
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/204:38 pmBTR - MDW
1 stop5h 11mDelta
sáb. 8/2310:11 amMDW - BTR
1 stop5h 42mDelta
Deal found 6/12$249
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 7/265:18 pmBTR - ORD
1 stop6h 51mDelta
jue. 7/315:35 amORD - BTR
1 stop6h 00mDelta
Deal found 6/12$249

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 junio 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

mié. 7/2

11:49 am-8:23 pm

1 stop8h 34m

Chicago O'Hare Intl

mié. 7/9

10:00 am-4:29 pm

1 stop6h 29m

$209

MobileChicago

MOB - ORD

MOBORD

Mobile

mar. 7/15

4:37 pm-9:31 pm

1 stop4h 54m

Chicago O'Hare Intl

mié. 7/30

6:00 am-11:53 am

1 stop5h 53m

$211

MemphisChicago

MEM - MDW

MEMMDW

Memphis

vie. 8/22

3:35 pm-10:00 pm

1 stop6h 25m

Chicago Midway

dom. 8/24

8:10 am-9:45 am

Nonstop1h 35m

$211

MemphisChicago

MEM - ORD

MEMORD

Memphis

vie. 8/29

7:30 am-9:31 am

Nonstop2h 01m

Chicago O'Hare Intl

lun. 9/1

8:58 am-10:58 am

Nonstop2h 00m

$214

MemphisChicago

MEM - ORD

MEMORD

Memphis

mié. 7/2

5:05 pm-7:24 pm

Nonstop2h 19m

Chicago O'Hare Intl

mié. 7/9

10:11 pm-12:07 am

Nonstop1h 56m

$216

MemphisChicago

MEM - ORD

MEMORD

Memphis

sáb. 8/30

11:10 am-4:28 pm

1 stop5h 18m

Chicago O'Hare Intl

dom. 8/31

5:45 am-10:25 am

1 stop4h 40m

$218

MemphisChicago

MEM - MDW

MEMMDW

Memphis

sáb. 8/30

12:20 pm-5:37 pm

1 stop5h 17m

Chicago Midway

dom. 8/31

6:00 am-10:25 am

1 stop4h 25m

$218

MobileChicago

MOB - ORD

MOBORD

Mobile

sáb. 8/30

12:30 pm-7:19 pm

1 stop6h 49m

Chicago O'Hare Intl

dom. 8/31

5:45 am-11:33 am

1 stop5h 48m

$221

MemphisChicago

MEM - ORD

MEMORD

Memphis

lun. 7/21

10:06 pm-2:13 pm

1 stop16h 07m

Chicago O'Hare Intl

mar. 7/22

4:36 pm-4:29 pm

1 stop23h 53m

$232

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

mié. 7/9

6:36 pm-11:57 pm

1 stop5h 21m

Chicago O'Hare Intl

mar. 7/15

1:23 pm-7:11 pm

1 stop5h 48m

$249

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 59 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 junio 12, 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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated junio 12, 2025.
See what other customers who have flown with Southwest, Delta and United Airlines from Mississippi to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.3
Good
725 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 United Airlines. According to our data, you can fly for as low as $64. Users have also found prices from $64 and $89 on Southwest 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, 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 Mississippi?

Book flights to Mississippi if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$469FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$258Average$431FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$338Average$396FlexibilityNo cancel feeOn-time63%

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