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$69+ 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 9/18. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$201
(FlightHub)

One-way from

$69
(United Airlines)

Popular in

January

Cheapest in

May

Average price

$464
From Mississippi to Chicago (CHI)
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One-way flight from Mississippi to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($23 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 July 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 July 3, 2025.

This FlightHub deal was found by Cheapflights users on 7/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/147:00 amMEM - ORD
1 stop9h 10mSpirit Airlines
Mon 8/186:00 amORD - MEM
1 stop8h 23mSpirit Airlines
Deal found 7/1$201
This Southwest deal was found by Cheapflights users on 7/1. 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.
Thu 8/143:35 pmMEM - MDW
1 stop6h 25mSouthwest
Sun 8/179:00 amMDW - MEM
1 stop4h 20mSouthwest
Deal found 7/1$203
This American Airlines deal was found by Cheapflights users on 7/2. 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.
Mon 8/114:49 pmMEM - ORD
Nonstop1h 46mAmerican Airlines
Thu 8/145:20 amORD - MEM
1 stop4h 54mAmerican Airlines
Deal found 7/2$207
This Southwest deal was found by Cheapflights users on 7/1. 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 8/1112:20 pmMEM - ORD
2 stops9h 10mSouthwest
Fri 8/1512:40 pmORD - MEM
1 stop8h 20mSouthwest
Deal found 7/1$208
This Delta deal was found by Cheapflights users on 7/2. 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 8/166:00 amMOB - ORD
1 stop6h 17mDelta
Sat 8/235:45 amORD - MOB
1 stop5h 42mDelta
Deal found 7/2$211
This Delta deal was found by Cheapflights users on 7/1. 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 7/2912:06 pmMEM - MDW
1 stop5h 33mDelta
Tue 8/59:25 amMDW - MEM
1 stop3h 58mDelta
Deal found 7/1$214
This Delta deal was found by Cheapflights users on 7/2. 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.
Thu 8/77:30 amMEM - ORD
1 stop6h 49mDelta
Mon 8/112:00 pmORD - MEM
1 stop6h 57mDelta
Deal found 7/2$218
This Mytrip deal was found by Cheapflights users on 6/30. 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.
Wed 8/277:00 amMEM - ORD
1 stop9h 10mMultiple Airlines
Wed 8/278:12 pmORD - MEM
1 stop11h 35mMultiple Airlines
Deal found 6/30$220
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Fri 8/19:54 amMEM - ORD
Nonstop2h 04mUnited Airlines
Thu 8/78:57 amORD - MEM
Nonstop2h 05mUnited Airlines
Deal found 7/1$224
This Delta deal was found by Cheapflights users on 7/1. 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 8/127:43 amJAN - ORD
1 stop4h 33mDelta
Tue 8/191:30 pmORD - JAN
1 stop7h 07mDelta
Deal found 7/1$237
This Delta deal was found by Cheapflights users on 6/30. 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 8/127:43 amJAN - MDW
1 stop4h 05mDelta
Tue 8/196:04 amMDW - JAN
1 stop4h 42mDelta
Deal found 6/30$237
This Delta deal was found by Cheapflights users on 7/2. 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 8/164:31 pmMOB - MDW
1 stop4h 41mDelta
Sat 8/236:04 amMDW - MOB
1 stop5h 23mDelta
Deal found 7/2$245

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 July 3, 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

Thu 8/14

7:00 am-4:10 pm

1 stop9h 10m

Chicago O'Hare Intl

Mon 8/18

6:00 am-2:23 pm

1 stop8h 23m

$201

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Thu 8/14

3:35 pm-10:00 pm

1 stop6h 25m

Chicago Midway

Sun 8/17

9:00 am-1:20 pm

1 stop4h 20m

$203

MemphisChicago

MEM - ORD

MEMORD

Memphis

Mon 8/11

4:49 pm-6:35 pm

Nonstop1h 46m

Chicago O'Hare Intl

Thu 8/14

5:20 am-10:14 am

1 stop4h 54m

$207

MemphisChicago

MEM - ORD

MEMORD

Memphis

Mon 8/11

12:20 pm-9:30 pm

2 stops9h 10m

Chicago O'Hare Intl

Fri 8/15

12:40 pm-9:00 pm

1 stop8h 20m

$208

MobileChicago

MOB - ORD

MOBORD

Mobile

Sat 8/16

6:00 am-12:17 pm

1 stop6h 17m

Chicago O'Hare Intl

Sat 8/23

5:45 am-11:27 am

1 stop5h 42m

$211

MemphisChicago

MEM - MDW

MEMMDW

Memphis

Tue 9/2

2:21 pm-9:26 pm

1 stop7h 05m

Chicago Midway

Wed 9/10

6:00 am-10:25 am

1 stop4h 25m

$213

MemphisChicago

MEM - ORD

MEMORD

Memphis

Thu 8/7

7:30 am-2:19 pm

1 stop6h 49m

Chicago O'Hare Intl

Mon 8/11

2:00 pm-8:57 pm

1 stop6h 57m

$218

MemphisChicago

MEM - ORD

MEMORD

Memphis

Wed 8/27

7:00 am-4:10 pm

1 stop9h 10m

Chicago O'Hare Intl

Wed 8/27

8:12 pm-7:47 am

1 stop11h 35m

$220

MemphisChicago

MEM - ORD

MEMORD

Memphis

Fri 8/1

7:30 am-9:29 am

Nonstop1h 59m

Chicago O'Hare Intl

Tue 8/5

12:45 pm-2:44 pm

Nonstop1h 59m

$224

JacksonChicago

JAN - ORD

JANORD

Jackson-Evers Intl

Tue 8/12

7:43 am-12:16 pm

1 stop4h 33m

Chicago O'Hare Intl

Tue 8/19

1:30 pm-8:37 pm

1 stop7h 07m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 58 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 July 3, 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.

How much does it cost to fly round-trip from Mississippi to Chicago?

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 July 3, 2025.
Read through reviews of airlines operating flights from Mississippi to Chicago, such as Southwest, Delta, and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.2

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
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.2

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
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.2

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
8,861 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.2

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
708 reviews
Southwest
8.0
Very good
4,266 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.2

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
4,266 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.2

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 $69. Users have also found prices from $69 and $82 on Southwest and Spirit 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
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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$481FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$258Average$424FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$338Average$392FlexibilityNo cancel feeOn-time63%

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