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Flights from Gulfport to Chicago
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Book flight tickets from Gulfport to Chicago starting at CAD 213

For as little as CAD 213, you can take your next adventure to Chicago without breaking the bank. Choose between one-way and return tickets from Gulfport below.

  • One way
  • Round-trip
      • GPT17:30
        4h 36m
        1 stop
        MDW22:06
        Tue, Dec 24|Gulfport - Chicago|Delta Air Lines
        CAD 213CAD 370
        42% OFF
        42% OFF
        CAD 370CAD 213

        Choose Delta Air Lines flights from Gulfport to Chicago. The one-way connecting flight with Delta Air Lines departs from Gulfport Biloxi International Airport on Tue, Dec 24, arriving at Midway International Airport. One-way ticket prices start from CAD 213 including taxes and charges.

      • GPT17:15
        4h 51m
        1 stop
        MDW22:06
        Thu, Dec 26|Gulfport - Chicago|Delta Air Lines
        CAD 222CAD 370
        40% OFF
        40% OFF
        CAD 370CAD 222

        Choose Delta Air Lines flights from Gulfport to Chicago. The one-way connecting flight with Delta Air Lines departs from Gulfport Biloxi International Airport on Thu, Dec 26, arriving at Midway International Airport. One-way ticket prices start from CAD 222 including taxes and charges.

      • GPT06:24
        5h 48m
        1 stop
        ORD12:12
        Tue, Dec 24|Gulfport - Chicago|American Airlines
        CAD 259CAD 370
        30% OFF
        30% OFF
        CAD 370CAD 259

        Choose American Airlines flights from Gulfport to Chicago. The one-way connecting flight with American Airlines departs from Gulfport Biloxi International Airport on Tue, Dec 24, arriving at O'Hare International Airport. One-way ticket prices start from CAD 259 including taxes and charges.

      • GPT07:06
        7h 34m
        1 stop
        ORD14:40
        Tue, Dec 24|Gulfport - Chicago|United Airlines
        CAD 261
        CAD 261

        Choose United Airlines flights from Gulfport to Chicago. The one-way connecting flight with United Airlines departs from Gulfport Biloxi International Airport on Tue, Dec 24, arriving at O'Hare International Airport. One-way ticket prices start from CAD 261 including taxes and charges.

      • GPT17:15
        6h 38m
        1 stop
        ORD23:53
        Thu, Dec 19|Gulfport - Chicago|Delta Air Lines
        CAD 297
        CAD 297

        Choose Delta Air Lines flights from Gulfport to Chicago. The one-way connecting flight with Delta Air Lines departs from Gulfport Biloxi International Airport on Thu, Dec 19, arriving at O'Hare International Airport. One-way ticket prices start from CAD 297 including taxes and charges.

      • GPT17:51
        5h 18m
        1 stop
        ORD23:09
        Thu, Dec 26|Gulfport - Chicago|American Airlines
        CAD 308
        CAD 308

        Choose American Airlines flights from Gulfport to Chicago. The one-way connecting flight with American Airlines departs from Gulfport Biloxi International Airport on Thu, Dec 26, arriving at O'Hare International Airport. One-way ticket prices start from CAD 308 including taxes and charges.

      • GPT17:30
        6h 28m
        1 stop
        ORD23:58
        Fri, Dec 6|Gulfport - Chicago|Delta Air Lines
        CAD 314
        CAD 314

        Choose Delta Air Lines flights from Gulfport to Chicago. The one-way connecting flight with Delta Air Lines departs from Gulfport Biloxi International Airport on Fri, Dec 6, arriving at O'Hare International Airport. One-way ticket prices start from CAD 314 including taxes and charges.

      • GPT06:10
        8h 2m
        1 stop
        ORD14:12
        Fri, Jan 3|Gulfport - Chicago|American Airlines
        CAD 315
        CAD 315

        Choose American Airlines flights from Gulfport to Chicago. The one-way connecting flight with American Airlines departs from Gulfport Biloxi International Airport on Fri, Jan 3, arriving at O'Hare International Airport. One-way ticket prices start from CAD 315 including taxes and charges.

      • GPT17:51
        6h 28m
        1 stop
        ORD00:19
        Sun, Jan 5|Gulfport - Chicago|American Airlines
        CAD 320
        CAD 320

        Choose American Airlines flights from Gulfport to Chicago. The one-way connecting flight with American Airlines departs from Gulfport Biloxi International Airport on Sun, Jan 5, arriving at O'Hare International Airport. One-way ticket prices start from CAD 320 including taxes and charges.

      • GPT17:15
        4h 5m
        1 stop
        ORD21:20
        Sun, Jan 5|Gulfport - Chicago|Delta Air Lines
        CAD 323
        CAD 323

        Choose Delta Air Lines flights from Gulfport to Chicago. The one-way connecting flight with Delta Air Lines departs from Gulfport Biloxi International Airport on Sun, Jan 5, arriving at O'Hare International Airport. One-way ticket prices start from CAD 323 including taxes and charges.

      • GPT13:00
        3h 5m
        Nonstop
        CHI14:00
        Thu, Dec 12|Gulfport - Chicago|Delta Air Lines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Find the best time to fly from Gulfport to Chicago

Price trend charts are a great way of tracking how much your flights cost in the lead up to departure and can help you choose when to book your tickets. See how prices to Chicago from Gulfport have changed and are set to move below.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Airlines Flying from Gulfport to Chicago

Compare prices from various providers below to understand which option best suits your travel needs, before enjoying a comfortable journey with a trusted airline from Gulfport to Chicago.

Delta Air Lines
From CAD 213
American Airlines
From CAD 259
United Airlines
From CAD 261

Find more flights and airlines

Alternative Routes from Gulfport to Chicago

Searching for potential routes that might be cheaper and faster? There are a few alternative ways to get to Chicago from Gulfport which could help you save money and time.

  • Cheapest
    Delta Air Lines
    GPT
    17:30
    6h 26m
    1 transfer
    ORD
    23:56
    Gulfport Biloxi International Airport - O'Hare International Airport
    Tue, Dec 24Delta Air Lines
    CAD 213
  • Delta Air Lines
    GPT
    17:30
    4h 36m
    1 transfer
    MDW
    22:06
    Gulfport Biloxi International Airport - Midway International Airport
    Tue, Dec 24Delta Air Lines
    CAD 213
  • Delta Air Lines
    GPT
    17:30
    4h 36m
    1 transfer
    MDW
    22:06
    Gulfport Biloxi International Airport - Midway International Airport
    Tue, Dec 24Delta Air Lines
    CAD 213
    Find More Flights

FAQ

  • When are flight tickets from Gulfport (GPT) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Gulfport to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Gulfport (GPT) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around CAD 546.

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.

How to find a cheap flight from Gulfport to Chicago

If you don’t know some of the key things to look out for when buying flight tickets, prices can often end up sky high or, worse, sold out! We’ve carefully compiled our six most important steps to help ensure you’re getting the best deals when planning your next journey.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Information from Gulfport to Chicago

Cheapest nonstop flight priceCAD 213
Off-season for travelNovember
Peak season for travelJanuary
Flight distance1,281.5 km
Popular airlineAmerican Airlines

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