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$99+ 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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Apr 27 — May 41
Sun 4/27
Sun 5/4
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 April 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$217
(United Airlines)

One-way from

$99
(Frontier)

Popular in

January

Cheapest in

October

Average price

$426
Provider with most accurate pricing for Jackson-Evers Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Jackson-Evers Intl-Chicago (CHI) flights.
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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. 8% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 22, 2025.

This United Airlines deal was found by Cheapflights users on 4/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/196:12 pmMEM - ORD
Nonstop1h 59mUnited Airlines
Fri 5/238:30 pmORD - MEM
Nonstop2h 00mUnited Airlines
Deal found 4/21$217
This Southwest deal was found by Cheapflights users on 4/21. 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.
Mon 5/195:05 amMEM - MDW
Nonstop1h 35mSouthwest
Mon 5/269:50 pmMDW - MEM
Nonstop1h 40mSouthwest
Deal found 4/21$217
This Delta deal was found by Cheapflights users on 4/22. 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.
Wed 5/217:31 pmMOB - ORD
1 stop4h 27mDelta
Sun 5/259:39 amORD - MOB
1 stop4h 34mDelta
Deal found 4/22$219
This Frontier deal was found by Cheapflights users on 4/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/55:00 pmMEM - ORD
1 stop6h 59mFrontier
Sun 6/86:00 amORD - MEM
1 stop9h 59mFrontier
Deal found 4/22$220
This Delta deal was found by Cheapflights users on 4/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/285:27 pmBTR - ORD
1 stop6h 31mDelta
Thu 6/57:05 amORD - BTR
1 stop6h 03mDelta
Deal found 4/21$224
This Mytrip deal was found by Cheapflights users on 4/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/175:14 pmMEM - ORD
1 stop6h 15mSpirit Airlines
Tue 5/209:02 pmORD - MEM
1 stop23h 11mSpirit Airlines
Deal found 4/22$225
This Booking.com deal was found by Cheapflights users on 4/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/43:05 pmMEM - ORD
1 stop8h 36mMultiple Airlines
Tue 5/137:47 amORD - MEM
1 stop8h 32mMultiple Airlines
Deal found 4/22$232
This Delta deal was found by Cheapflights users on 4/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/136:00 amBTR - MDW
1 stop5h 53mDelta
Sat 5/2410:25 amMDW - BTR
1 stop5h 27mDelta
Deal found 4/20$233
This American Airlines deal was found by Cheapflights users on 4/21. 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.
Wed 5/217:00 amMEM - ORD
Nonstop1h 55mAmerican Airlines
Mon 5/263:15 pmORD - MEM
Nonstop1h 49mAmerican Airlines
Deal found 4/21$236
This Delta deal was found by Cheapflights users on 4/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/196:37 amMEM - MDW
1 stop5h 51mDelta
Fri 5/236:00 amMDW - MEM
1 stop5h 27mDelta
Deal found 4/21$237
This Delta deal was found by Cheapflights users on 4/22. 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.
Sat 5/2411:50 amMEM - ORD
1 stop5h 16mDelta
Sun 5/256:40 amORD - MEM
1 stop6h 36mDelta
Deal found 4/22$247
This Delta deal was found by Cheapflights users on 4/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/216:00 pmGPT - ORD
1 stop5h 55mDelta
Sat 7/265:55 pmORD - GPT
1 stop4h 11mDelta
Deal found 4/21$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 April 22, 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

Mon 5/19

6:12 pm-8:11 pm

Nonstop1h 59m

Chicago O'Hare Intl

Fri 5/23

8:30 pm-10:30 pm

Nonstop2h 00m

$217

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Mon 5/19

5:05 am-6:40 am

Nonstop1h 35m

Chicago Midway

Mon 5/26

9:50 pm-11:30 pm

Nonstop1h 40m

$217

MobileChicago

MOB - ORD

MOBORD

Mobile

Wed 5/21

7:31 pm-11:58 pm

1 stop4h 27m

Chicago O'Hare Intl

Sun 5/25

9:39 am-2:13 pm

1 stop4h 34m

$219

MemphisChicago

MEM - ORD

MEMORD

Memphis

Thu 6/5

5:00 pm-11:59 pm

1 stop6h 59m

Chicago O'Hare Intl

Sun 6/8

6:00 am-3:59 pm

1 stop9h 59m

$220

Baton RougeChicago

BTR - ORD

BTRORD

Baton Rouge Ryan

Wed 5/28

5:27 pm-11:58 pm

1 stop6h 31m

Chicago O'Hare Intl

Mon 6/2

7:05 am-1:08 pm

1 stop6h 03m

$224

MemphisChicago

MEM - ORD

MEMORD

Memphis

Sat 5/17

5:14 pm-11:29 pm

1 stop6h 15m

Chicago O'Hare Intl

Tue 5/20

9:02 pm-8:13 pm

1 stop23h 11m

$225

MemphisChicago

MEM - ORD

MEMORD

Memphis

Sun 5/4

3:05 pm-11:41 pm

1 stop8h 36m

Chicago O'Hare Intl

Tue 5/13

7:47 am-4:19 pm

1 stop8h 32m

$232

Baton RougeChicago

BTR - MDW

BTRMDW

Baton Rouge Ryan

Tue 5/13

6:00 am-11:53 am

1 stop5h 53m

Chicago Midway

Sat 5/24

10:25 am-3:52 pm

1 stop5h 27m

$233

MemphisChicago

MEM - ORD

MEMORD

Memphis

Wed 5/21

7:00 am-8:55 am

Nonstop1h 55m

Chicago O'Hare Intl

Mon 5/26

3:15 pm-5:04 pm

Nonstop1h 49m

$236

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Mon 5/19

6:37 am-12:28 pm

1 stop5h 51m

Chicago Midway

Fri 5/23

6:00 am-11:27 am

1 stop5h 27m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 53 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 April 22, 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 April 22, 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
4,286 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,286 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,683 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,286 reviews

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 Frontier. According to our data, you can fly for as low as $99. Users have also found prices from $100 and $109 on Delta and United Airlines, 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 $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
Hammond
Benton Harbor
Porter
Lansing
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.
LaGuardia to O'Hare Intl flights
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Philadelphia to O'Hare Intl flights
Boston to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
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Ontario to O'Hare Intl flights
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San Francisco to Midway flights
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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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$459FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$281Average$462FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$338Average$396FlexibilityNo cancel feeOn-time63%

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