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$179+ Cheap flights from Biloxi, MS 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 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
MSY — CHI
May 1 — May 81
Fri 5/1
Fri 5/8
1 adult, Economy
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Cheap flight deals from Biloxi to Chicago

Cheapest flights from Biloxi to Chicago
Explore the most affordable flight options available from Biloxi to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 1, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:20 pm
GPT
-
ORD
2 stops15h 03m
Multiple Airlines
Sat 5/24:50 pm
ORD
-
GPT
1 stop25h 50m
Multiple Airlines
Deal found 3/28$244
This Delta deal was found by Cheapflights users on 3/29. 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 5/26:00 am
GPT
-
MDW
1 stop4h 14m
Delta
Sat 5/96:23 am
MDW
-
GPT
1 stop7h 16m
Delta
Deal found 3/29$291
This Delta deal was found by Cheapflights users on 3/29. 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 5/23:00 pm
GPT
-
ORD
1 stop5h 16m
Delta
Sat 5/97:05 am
ORD
-
GPT
1 stop6h 34m
Delta
Deal found 3/29$291
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:54 pm
GPT
-
ORD
1 stop17h 29m
Multiple Airlines
Thu 5/77:00 am
ORD
-
GPT
2 stops12h 10m
Multiple Airlines
Deal found 3/30$294
This Delta deal was found by Cheapflights users on 3/29. 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 4/305:55 pm
GPT
-
MDW
1 stop4h 33m
Delta
Sat 5/25:21 pm
MDW
-
GPT
1 stop4h 52m
Delta
Deal found 3/29$310
This Delta deal was found by Cheapflights users on 3/27. 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 7/86:00 pm
GPT
-
ORD
1 stop5h 53m
Delta
Mon 7/139:45 am
ORD
-
GPT
1 stop7h 30m
Delta
Deal found 3/27$310
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:20 pm
GPT
-
ORD
1 stop13h 45m
Multiple Airlines
Thu 5/76:50 am
ORD
-
GPT
2 stops24h 51m
Multiple Airlines
Deal found 3/31$321
This Delta deal was found by Cheapflights users on 3/30. 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.
Thu 8/276:00 pm
GPT
-
ORD
1 stop5h 57m
Delta
Sun 8/309:30 am
ORD
-
GPT
1 stop4h 03m
Delta
Deal found 3/30$329
This Delta deal was found by Cheapflights users on 3/28. 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 8/56:00 pm
GPT
-
ORD
1 stop5h 53m
Delta
Sun 8/95:15 am
ORD
-
GPT
1 stop4h 04m
Delta
Deal found 3/28$335
This Delta deal was found by Cheapflights users on 3/30. 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 4/145:55 pm
GPT
-
ORD
1 stop4h 26m
Delta
Sat 4/185:15 am
ORD
-
GPT
1 stop4h 09m
Delta
Deal found 3/30$339
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:54 pm
GPT
-
ORD
2 stops16h 39m
Multiple Airlines
Sun 4/266:00 am
ORD
-
GPT
1 stop12h 40m
Multiple Airlines
Deal found 3/29$345
This Delta deal was found by Cheapflights users on 3/29. 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 8/66:30 am
GPT
-
ORD
1 stop6h 04m
Delta
Sun 8/95:15 am
ORD
-
GPT
1 stop4h 04m
Delta
Deal found 3/29$354

Find flight deals from Biloxi to Chicago

Keep the following information in mind while searching for Biloxi to Chicago flight deals. Data was last updated April 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$244
(Kiwi.com)

One-way from

$179
(Delta)

Popular in

June

Cheapest in

November

Average price

$253
Provider with most accurate pricing for Gulfport Biloxi Regional-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Gulfport Biloxi Regional-Chicago (CHI) flights.
Search Deals
From Biloxi to Chicago (CHI)
Search Deals
One-way flight from Biloxi to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($70 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Biloxi 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 1, 2026.
Use the filters below to find and compare flights from Biloxi to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Sat 5/2

6:00 am-10:14 am

1 stop4h 14m

Chicago Midway

Sat 5/9

6:23 am-1:39 pm

1 stop7h 16m

$291

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Sat 5/2

3:00 pm-8:16 pm

1 stop5h 16m

Chicago O'Hare Intl

Sat 5/9

7:05 am-1:39 pm

1 stop6h 34m

$291

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 5/15

6:09 pm-11:54 pm

1 stop5h 45m

Chicago O'Hare Intl

Tue 5/19

3:26 pm-11:26 pm

1 stop8h 00m

$310

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Wed 8/12

6:00 pm-11:57 pm

1 stop5h 57m

Chicago O'Hare Intl

Mon 8/17

8:15 am-1:33 pm

1 stop5h 18m

$310

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Wed 8/5

6:00 pm-11:53 pm

1 stop5h 53m

Chicago O'Hare Intl

Sun 8/9

5:15 am-9:19 am

1 stop4h 04m

$335

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Wed 4/15

5:55 pm-11:59 pm

1 stop6h 04m

Chicago O'Hare Intl

Sun 4/19

5:15 am-9:24 am

1 stop4h 09m

$339

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Fri 4/24

6:54 pm-11:33 am

2 stops16h 39m

Chicago O'Hare Intl

Sun 4/26

6:00 am-6:40 pm

1 stop12h 40m

$345

GulfportChicago

GPT - ORD

GPTORD

Gulfport Biloxi Regional

Thu 8/6

6:30 am-12:34 pm

1 stop6h 04m

Chicago O'Hare Intl

Sun 8/9

5:15 am-9:19 am

1 stop4h 04m

$354

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Wed 8/12

10:30 am-4:27 pm

1 stop5h 57m

Chicago Midway

Mon 8/17

5:25 pm-10:06 pm

1 stop4h 41m

$384

GulfportChicago

GPT - MDW

GPTMDW

Gulfport Biloxi Regional

Thu 4/30

5:55 pm-10:28 pm

1 stop4h 33m

Chicago Midway

Mon 5/4

5:21 pm-10:13 pm

1 stop4h 52m

$423

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/29

Showing 1-10 of 27 resultsSorted by cheapest first
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2
3

Best time to book a flight from Biloxi to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Biloxi 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 Biloxi to Chicago

What is the cheapest month to book a flight from Biloxi to Chicago?

Currently, February is the cheapest month in which you can book a flight from Biloxi to Chicago (average of $48). Flying from Biloxi to Chicago in December is currently the most expensive (average of $159). 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 B1L to CHI?

Find hourly flight availability from Biloxi 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 1, 2026.

It’s typically best to fly out from Biloxi to Chicago in the afternoon. Doing so could potentially save you 29% on the flight price compared to flying in the evening, which is usually more expensive.

What is the cheapest day to fly from Biloxi to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Biloxi to Chicago. Price data was last updated on March 28, 2026.

Travelers seeking maximum savings on their Biloxi to Chicago flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Biloxi to Chicago

Explore weekly flight availability from Biloxi to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 1, 2026.

The most flights from B1L to CHI are scheduled on a Tuesday (49 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (12 on average).

How much does it cost to fly round-trip from Biloxi 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 April 1, 2026.
Read through reviews of airlines operating flights from Biloxi to Chicago, such as American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.1
Good
11,545 reviews

Crew

7.9

Entertainment

6.9

Boarding

7.5

Food

6.4

Overall

7.1

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.1
Good
11,545 reviews
American Airlines
7.1
Good
11,545 reviews

Crew

7.9

Entertainment

6.9

Boarding

7.5

Food

6.4

Overall

7.1

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

Related info for your journey

Find useful and relevant information for your journey from Biloxi to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Biloxi to Chicago?

    Airlines like Delta and American Airlines fly from Biloxi to Chicago in about 4h 14m. The time it takes to get you to your destination can typically vary by up to 1h 31m. Biloxi and Chicago are separated by a distance of 789 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most reliable airlines from Biloxi to Chicago?

    Before booking your flight to Chicago from Biloxi, check out the most reliable airlines to get you to your destination on time: ANA (88%), Brussels Airlines (85%), Turkish Airlines( 82%).

  • What are the cheapest flights from Biloxi to Chicago?

    Looking at all options, your cheapest flight can be booked for $79. While the most popular route (Gulfport Biloxi Regional - Chicago O'Hare Intl) can be booked for $291 on average, our data indicates $671 when flying from Biloxi to Chicago.

  • Can I find deals for flights from Biloxi to Chicago that include hotel bookings?

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

  • How can I find direct flights from Biloxi to Chicago?

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

  • Can I find deals for business class flights from Biloxi to Chicago?

    Yes. Cheapflights offers flight deals from Biloxi 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 Biloxi to Chicago?

    Currently, February is the cheapest month in which you can book a flight from Biloxi to Chicago (average of $48). Flying from Biloxi to Chicago in December is currently the most expensive (average of $159). 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 Chicago?

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

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Top 6 airlines flying from Biloxi to Chicago

Discover the top 6 airlines that operate flights from Biloxi 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 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$18Average$195FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$77Average$164FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$133Average$274FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$163Average$369FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$173Average$273FlexibilityNo cancel feeOn-time63%
DeltaCheapest$210Average$421FlexibilityNo cancel feeOn-timeN/A

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