GPT - CHI

$183 Find Cheap Flights from Gulfport to Chicago - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$301
Typical prices: $299-$470
American Airlines
Sat 11/10Wed 11/14
GPT - ORD • 1 stop
Cheapest one-way
$190
Typical prices: $229-$429
Multiple Airlines
Tue 11/13
GPT - ORD • 2 stops
Nonstop flights
Not available
There are currently no direct flights between Gulfport and Chicago. You'll need to take a connecting flight to reach the destination.
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Top routes
GPT - MDW
Cheapest • 15% average savings
GPT - ORD
Most popular
Insights
Insights
When to travel
November
Cheapest • 31% price drop
October
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Dallas/Fort Worth (DFW)
Cheapest • Avg $373 (round-trip)
Atlanta Hartsfield-Jackson (ATL)
Shortest trip • 5h 18m (one-way)
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Insights
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Flight Deals

Cheap Flights from Gulfport to Chicago (GPT-CHI)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Gulfport to Chicago

Tue, Nov 10 - Sat, Nov 14
American Airlines Logo
5:32 pm - 12:01 amGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
6h 29m1 stop Charlotte Douglas
American Airlines Logo
12:02 pm - 5:57 pmORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
5h 55m1 stop Dallas/Fort Worth
$301American Airlines
Wed, Nov 11 - Sat, Nov 14
Delta Logo
1:50 pm - 8:49 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
6h 59m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:30 pm - 8:43 pmORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
7h 13m1 stop Atlanta Hartsfield-Jackson
$301Delta
Tue, Nov 10 - Sat, Nov 14
Delta Logo
10:04 am - 5:05 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
7h 01m1 stop Atlanta Hartsfield-Jackson
Delta Logo
8:04 am - 2:21 pmORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
6h 17m1 stop Atlanta Hartsfield-Jackson
$301Delta
Sat, Oct 17 - Sat, Oct 24
Delta Logo
4:00 pm - 8:38 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
4h 38m1 stop Atlanta Hartsfield-Jackson
Delta Logo
8:05 am - 2:21 pmORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
6h 16m1 stop Atlanta Hartsfield-Jackson
$305Delta
Thu, Nov 12 - Mon, Nov 16
American Airlines Logo
6:19 am - 2:30 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
8h 11m1 stop Charlotte Douglas
American Airlines Logo
6:00 am - 11:11 amORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
5h 11m1 stop Dallas/Fort Worth
$319American Airlines
Fri, Nov 13 - Mon, Nov 16
American Airlines Logo
6:21 pm - 11:59 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
5h 38m1 stop Dallas/Fort Worth
American Airlines Logo
6:00 am - 11:11 amORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
5h 11m1 stop Dallas/Fort Worth
$319American Airlines
Fri, Oct 30 - Sun, Nov 1
American Airlines Logo
6:42 pm - 12:08 amGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
5h 26m1 stop Charlotte Douglas
American Airlines Logo
5:00 am - 11:11 amORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
6h 11m1 stop Dallas/Fort Worth
$319American Airlines
Wed, Oct 14 - Sat, Oct 17
United Airlines Logo
5:14 pm - 11:27 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
6h 13m1 stop Houston George Bush Intcntl
United Airlines Logo
6:25 am - 1:25 pmORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
7h 00m1 stop Houston George Bush Intcntl
$321United Airlines
Fri, Sep 25 - Tue, Sep 29
United Airlines Logo
5:14 pm - 11:26 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
6h 12m1 stop Houston George Bush Intcntl
United Airlines Logo
10:32 am - 4:12 pmORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
5h 40m1 stop Houston George Bush Intcntl
$349United Airlines
Sat, Nov 7 - Tue, Nov 10
United Airlines Logo
4:55 pm - 11:26 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
6h 31m1 stop Houston George Bush Intcntl
United Airlines Logo
2:22 pm - 7:34 pmORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
5h 12m1 stop Houston George Bush Intcntl
$381United Airlines
Booking Insights

Price, demand and travel trends for Gulfport to Chicago flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Gulfport to Chicago with more confidence.

How much is a round-trip flight from Gulfport to Chicago?

Round-trip flights from Gulfport to Chicago start at $301. Prices are typical for this route right now, with typical round-trip fares ranging from $299 to $470. The lowest price found in the past 5 days was $301 on American Airlines.

What is the cheapest Gulfport to Chicago flight route?

Gulfport (GPT) to Chicago Midway Airport (MDW) is the cheapest Gulfport to Chicago route, averaging $273 round-trip. Other Gulfport to Chicago routes average $368, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Gulfport to Chicago?

Tuesday is the cheapest day of the week to fly from Gulfport to Chicago, it is 17% cheaper than the average day. Sunday is the most expensive day with flight prices 156% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is the cheapest month to fly from Gulfport to Chicago?

  • November is the cheapest month to fly from Gulfport to Chicago at $248 round-trip.
  • December ($587) and May ($474) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 136% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

Find deals

Key details for Gulfport to Chicago flights

Low season

February

Cheapest flight

$190
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 23% lower on average.
Flight from Gulfport to Chicago O'Hare Intl Airport

When to book flights from Gulfport to Chicago

Are your dates flexible? Find out the best times to travel from Gulfport to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Gulfport to Chicago flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airports can I use when flying from Gulfport to Chicago?

    Flights from Gulfport to Chicago usually depart from Gulfport Biloxi Regional (GPT) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • What cabin classes can I book on flights from Gulfport to Chicago?

    Two cabin classes are available on flights from Gulfport to Chicago:

    • Economy Class
    • First Class

  • Which airports do connecting flights from Gulfport to Chicago pass through?

    One-stop flights from Gulfport to Chicago most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 48% of one-stop connections
    • Charlotte Douglas (CLT) - 30% of one-stop connections
    • Houston George Bush Intcntl (IAH) - 13% of one-stop connections
    • Dallas/Fort Worth (DFW) - 9% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Gulfport to Chicago?

    Yes. Being flexible with your travel dates can save you up to 68% on the Gulfport to Chicago route. Tuesday is the cheapest departure day at $299 round-trip on average, while Sunday is the most expensive at $920, a difference of $621. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What popular places can I visit in Chicago?

    Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago on KAYAK.

  • How long is a flight from Gulfport to Chicago?

    A nonstop flight from Gulfport to Chicago takes 0h 00m, covering 796 miles.

  • Do I need a passport to fly from Gulfport to Chicago?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

  • Have flight prices from Gulfport to Chicago changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $301 to $1,622. That means the highest observed fare was about 5x higher than the lowest one.

  • How are flight prices from Gulfport to Chicago looking right now?

    One-way fares from Gulfport to Chicago are currently lower than usual. Average one-way flight prices are about $235, which is 21% below the typical average for this route.

  • How much time can I save by choosing a different layover airport from Gulfport to Chicago?

    Flying via Atlanta Hartsfield-Jackson (ATL) gives the shortest average 1-stop total travel time at 5h 18m, compared with 5h 53m via Charlotte Douglas (CLT) and 5h 55m via Dallas/Fort Worth (DFW).

  • What car rental options are available in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Dollar
    • Ace

    Near Chicago Midway Airport (MDW) — daily rates from around $32:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

    Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

    • Alamo
    • Enterprise Rent-A-Car
    • Budget
    • Avis
    • National

  • How much should I expect to pay for a Gulfport to Chicago flight?

    Round-trip flights from Gulfport to Chicago range from $299 to $470, with an average of $359 over the past 12 months. Anything below $299 counts as a good deal.

Your guide to booking Gulfport to Chicago flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Tuesday departure instead of Sunday. On this route, Tuesday flights average $299 - about $621 less than Sunday (68% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Gulfport to Chicago trip for November. Fares historically average $248 round-trip in that month - typically $339 less than the most expensive month, which is December (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.
    - DoubleTree by Hilton Chicago Midway Airport
    - Holiday Inn Chicago - Midway Airport S by IHG
    - Skylark Motel

More options for your flight from Gulfport to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Car rentals in Chicago
Hotels in Chicago
Vacations in Chicago