To save up to 53% on this flight, we recommend booking at least 59 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Mississippi to Chicago from $347 1-2 weeks out and tickets from $517 for flights departing within the next 72 hours.
The best pricing can be found in the month of May. Prices to Chicago from Mississippi average $423. You can even find prices in May for less than $423, as users have found deals to Chicago from as low as $262. The month of March appears to be one of the more expensive times to travel to Chicago from Mississippi. Flying in the targeted month can save you up to 33%.
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.
Fly from
Fly to
Budget
$228 - $396
Route
Depart
Return
Price
Gulfport Biloxi RegionalChicago O'Hare Intl
GPT - ORD
GPTORD
Gulfport Biloxi Regional
Wed 8/21
1 stop5h 00m
Chicago O'Hare Intl
Sat 8/24
1 stop7h 14m
Gulfport Biloxi RegionalChicago O'Hare Intl
GPT - ORD
GPTORD
Gulfport Biloxi Regional
Wed 8/21
1 stop7h 03m
Chicago O'Hare Intl
Sat 8/24
2 stops6h 09m
Gulfport Biloxi RegionalChicago O'Hare Intl
GPT - ORD
GPTORD
Gulfport Biloxi Regional
Tue 6/18
1 stop4h 53m
Chicago O'Hare Intl
Sat 6/22
2 stops9h 57m
Gulfport Biloxi RegionalChicago O'Hare Intl
GPT - ORD
GPTORD
Gulfport Biloxi Regional
Wed 5/8
1 stop6h 03m
Chicago O'Hare Intl
Sat 5/11
1 stop6h 52m
Gulfport Biloxi RegionalChicago O'Hare Intl
GPT - ORD
GPTORD
Gulfport Biloxi Regional
Wed 5/8
1 stop6h 39m
Chicago O'Hare Intl
Sat 5/11
2 stops9h 40m
Jackson-Evers IntlChicago O'Hare Intl
JAN - ORD
JANORD
Jackson-Evers Intl
Wed 6/5
1 stop4h 40m
Chicago O'Hare Intl
Thu 6/6
1 stop7h 10m
Jackson-Evers IntlChicago O'Hare Intl
JAN - ORD
JANORD
Jackson-Evers Intl
Sat 7/6
1 stop5h 09m
Chicago O'Hare Intl
Sat 7/20
1 stop5h 25m
Jackson-Evers IntlChicago O'Hare Intl
JAN - ORD
JANORD
Jackson-Evers Intl
Wed 5/15
1 stop7h 26m
Chicago O'Hare Intl
Sun 5/19
1 stop5h 38m
Jackson-Evers IntlChicago Midway
JAN - MDW
JANMDW
Jackson-Evers Intl
Tue 4/30
1 stop9h 50m
Chicago Midway
Wed 5/1
1 stop12h 00m
No data available for this route at this time. Please check back soon.
Food
Entertainment
Comfort
Overall
Crew
Boarding
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Food
Entertainment
Comfort
Overall
Crew
Boarding
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Food
Entertainment
Comfort
Overall
Crew
Boarding
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Food
Entertainment
Comfort
Overall
Crew
Boarding
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Food
Entertainment
Comfort
Overall
Crew
Boarding
Reviews
I was traveling with a companion that utilizes a scooter to get around. We have flown together many times and used other airlines. Southwest by far is the most accommodating airline in the fleet your staff Makes the accessibility easy and convenient for for this type of travel. We would personally like to think the flight teams of our two flights for being very accommodating and helpful throughout our trip.
Cheapflights helps you search for flights from Mississippi to Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.
Cheapflights helps you find that perfect flight to Chicago from Mississippi by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!
Cheapflights does show flights with no change fees to all users. To see these options for flights from Mississippi to Chicago, users can toggle the no change fees filter when performing a flight search.
Yes! Start tracking prices for Mississippi to Chicago flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.