Illinois

$153+ Cheap flights from Mississippi to Illinois

JAN — ORD
Dec 4 — Dec 111
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Find cheap flights from Mississippi to Illinois with Cheapflights

1. Tell us where you want to go

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Cheap flight deals from Mississippi to Illinois

Cheapest flights from Mississippi to Illinois

Wed 12/21:24 pm -
1 stop5h 45m
Fri 12/46:16 pm -
1 stop4h 49m
Deal found 10/30$309
Wed 12/211:14 am -
1 stop5h 02m
Fri 12/46:00 am -
1 stop4h 29m
Deal found 10/30$309
Sat 12/193:35 pm -
1 stop8h 50m
Fri 12/2512:45 pm -
1 stop4h 50m
Deal found 11/2$314
Thu 12/106:15 pm -
1 stop4h 55m
Mon 12/147:35 am -
2 stops10h 00m
Deal found 11/2$320
Tue 12/16:09 pm -
1 stop4h 45m
Tue 12/86:00 am -
1 stop7h 11m
Deal found 10/31$321
Tue 12/16:28 pm -
1 stop5h 52m
Tue 12/88:10 am -
1 stop5h 07m
Deal found 10/31$321
Tue 12/16:09 pm -
1 stop5h 47m
Tue 12/811:35 am -
2 stops10h 22m
Deal found 10/31$326
Wed 12/93:48 pm -
1 stop5h 05m
Mon 12/146:16 pm -
1 stop4h 49m
Deal found 11/3$327
Tue 12/15:11 pm -
1 stop5h 43m
Tue 12/86:00 am -
1 stop4h 29m
Deal found 11/3$327
Sat 11/215:01 pm -
1 stop5h 32m
Mon 11/235:00 am -
1 stop6h 45m
Deal found 11/2$328
Thu 12/31:54 pm -
1 stop5h 15m
Wed 12/910:36 am -
1 stop6h 48m
Deal found 11/2$330
Wed 12/210:04 am -
2 stops8h 22m
Wed 12/911:35 am -
2 stops10h 22m
Deal found 11/2$331

Find flight deals from Mississippi to Illinois

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$309
(Delta)

One-way from

$153
(Kiwi.com)

Popular in

June

Cheapest in

April

Average price

$366
Provider with most accurate pricing for Jackson-Evers Intl-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Jackson-Evers Intl-Chicago (CHI) flights.
From Mississippi to Illinois
One-way flight from Mississippi to Illinois
Highest demand for flights based on searches. 17% potential increase in price ($101 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).
Average for round-trip flights in November 2026

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Mississippi to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

GulfportChicago

GPT Gulfport Biloxi Regional - ORD Chicago O'Hare Intl

GPTORD

Gulfport Biloxi Regional

Fri 12/11

6:46 pm-10:00 pm

2 stops27h 14m

Chicago O'Hare Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$153
Quickest round-trip

JacksonChicago

JAN Jackson-Evers Intl - MDW Chicago Midway

JANMDW

Jackson-Evers Intl

Tue 11/24

8:15 pm-1:00 am

1 stop4h 45m

Chicago Midway

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$155

GulfportChicago

GPT Gulfport Biloxi Regional - MDW Chicago Midway

GPTMDW

Gulfport Biloxi Regional

Fri 12/11

6:46 pm-11:33 am

3 stops16h 47m

Chicago Midway

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$186

JacksonChicago

JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl

JANORD

Jackson-Evers Intl

Wed 11/18

5:06 pm-11:54 pm

1 stop6h 48m

Chicago O'Hare Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$208

JacksonChicago

JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl

JANORD

Jackson-Evers Intl

Sun 4/11

2:40 pm-9:10 pm

1 stop6h 30m

Chicago O'Hare Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$209

JacksonChicago

JAN Jackson-Evers Intl - ORD Chicago O'Hare Intl

JANORD

Jackson-Evers Intl

Mon 4/12

6:59 pm-11:50 pm

1 stop4h 51m

Chicago O'Hare Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$209

JacksonChicago

JAN Jackson-Evers Intl - MDW Chicago Midway

JANMDW

Jackson-Evers Intl

Fri 1/1

1:10 pm-10:45 pm

1 stop9h 35m

Chicago Midway

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$214

JacksonChicago

JAN Jackson-Evers Intl - MDW Chicago Midway

JANMDW

Jackson-Evers Intl

Mon 4/12

5:45 am-3:15 pm

2 stops9h 30m

Chicago Midway

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$214

GulfportChicago

GPT Gulfport Biloxi Regional - MDW Chicago Midway

GPTMDW

Gulfport Biloxi Regional

Sun 12/13

6:15 am-12:04 pm

1 stop5h 49m

Chicago Midway

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$221

GulfportChicago

GPT Gulfport Biloxi Regional - MDW Chicago Midway

GPTMDW

Gulfport Biloxi Regional

Fri 12/11

6:09 pm-10:54 pm

1 stop4h 45m

Chicago Midway

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$221

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Mississippi to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Mississippi with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Mississippi to Illinois

What is the cheapest month to book a flight from Mississippi to Illinois?

Currently, January is the cheapest month in which you can book a flight from Mississippi to Illinois (average of $358). Flying from Mississippi to Illinois in June is currently the most expensive (average of $700). 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.

Reviews of airlines servicing Illinois

Read reviews from past customers who have flown Southwest,Delta, andAmerican Airlines from Mississippi to Illinois. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Related info for your journey

  • How long is the flight from Mississippi to Illinois?

    There are many flights that can get you from Mississippi to Illinois in 4h 55m. Fly via Delta, Southwest, or American Airlines to get the fastest option. Mississippi and Illinois are separated by a distance of 667 mi. This flight may include one or multiple stops.

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

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $151. Users have also found prices from $154 and $169 on Southwest and American Airlines, respectively.

  • Can I find deals for flights from Mississippi to Illinois that include hotel bookings?

    Yes. In addition to deals on Mississippi to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Mississippi to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Mississippi to Illinois.

  • Can I find deals for business class flights from Mississippi to Illinois?

    Yes. Cheapflights offers flight deals from Mississippi to Illinois 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 Illinois?

    Currently, January is the cheapest month in which you can book a flight from Mississippi to Illinois (average of $358). Flying from Mississippi to Illinois in June is currently the most expensive (average of $700). 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

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Mississippi to Illinois

Top 3 airlines flying from Mississippi to Illinois

AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$286Average$409FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$296Average$502FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$308Average$462FlexibilityNo cancel feeOn-time63%

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