GPT - CHI

$170 Find Cheap Flights from Gulfport to Chicago - Compare and Save

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Everything you should know

Cheapest round-trip
$255
Typical prices: $315-$587
Multiple Airlines
Mon 2/19Tue 2/27
GPT - ORD • 2 stops
Cheapest one-way
$170
Typical prices: $230-$461
Multiple Airlines
Tue 12/11
GPT - MDW • 3 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.
Insights
Insights
Top routes
GPT - MDW
Cheapest • 15% average savings
GPT - ORD
Most popular
Insights
Insights
When to travel
November
Cheapest • 36% price drop
December
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Houston George Bush Intcntl (IAH)
Cheapest • Avg $392 (round-trip)
Atlanta Hartsfield-Jackson (ATL)
Shortest trip • 5h 10m (one-way)
Insights
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

Fri, Feb 19 - Sat, Feb 27
Multiple Airlines Logo
6:46 pm - 4:14 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
21h 28m2 stops Tampa Fort Lauderdale
Multiple Airlines Logo
5:16 pm - 7:10 pmORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
25h 54m1 stop Orlando
$255Multiple Airlines
Fri, Feb 19 - Sat, Feb 27
Multiple Airlines Logo
6:46 pm - 11:46 pmGPT  Gulfport Biloxi Regional-MDW Chicago Midway
29h 00m2 stops Tampa Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:47 pm - 7:10 pmMDW  Chicago Midway-GPT Gulfport Biloxi Regional
22h 23m1 stop Orlando
$271Multiple Airlines
Fri, Feb 19 - Sat, Feb 27
Multiple Airlines Logo
6:46 pm - 9:13 amGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
14h 27m1 stop Tampa
Multiple Airlines Logo
5:16 pm - 7:10 pmORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
25h 54m1 stop Orlando
$321Multiple Airlines
Fri, Dec 18 - Sat, Dec 19
Delta Logo
6:09 pm - 11:56 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
5h 47m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:25 am - 9:50 amORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
4h 25m1 stop Atlanta Hartsfield-Jackson
$330Delta
Thu, Dec 17 - Sat, Dec 19
Delta Logo
1:52 pm - 7:09 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
5h 17m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:25 am - 9:50 amORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
4h 25m1 stop Atlanta Hartsfield-Jackson
$330Delta
Wed, Dec 23 - Mon, Jan 4
Delta Logo
5:20 pm - 12:02 amGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
6h 42m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:50 am - 4:01 pmORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
6h 11m1 stop Atlanta Hartsfield-Jackson
$330Delta
Wed, Dec 23 - Sun, Jan 3
Delta Logo
5:20 pm - 12:02 amGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
6h 42m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:25 am - 1:55 pmORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
7h 30m1 stop Atlanta Hartsfield-Jackson
$330Delta
Wed, Dec 23 - Mon, Jan 4
Delta Logo
5:20 pm - 12:02 amGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
6h 42m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:45 pm - 10:08 pmORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
8h 23m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
$335Delta
Fri, Nov 20 - Mon, Nov 23
American Airlines Logo
6:28 pm - 12:20 amGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
5h 52m1 stop Dallas/Fort Worth
American Airlines Logo
4:58 pm - 12:01 amORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
7h 03m1 stop Charlotte Douglas
$339American Airlines
Fri, Nov 20 - Mon, Nov 23
American Airlines Logo
5:49 pm - 11:59 pmGPT  Gulfport Biloxi Regional-ORD Chicago O'Hare Intl
6h 10m1 stop Charlotte Douglas
American Airlines Logo
5:00 am - 11:20 amORD  Chicago O'Hare Intl-GPT Gulfport Biloxi Regional
6h 20m1 stop Dallas/Fort Worth
$339American 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 with more confidence.

What is the cheapest Gulfport to Chicago flight route?

Gulfport (GPT) to Chicago Midway Airport (MDW) is the cheapest Gulfport to Chicago route, averaging $299 round-trip. Other Gulfport to Chicago routes average $404, based on KAYAK data over the past 12 months.

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

Based on deals KAYAK users found in the last 12 months, Tuesday is the cheapest day of the week to fly from Gulfport to Chicago. It’s 24% cheaper than the average day, while Sunday is the most expensive, with prices 135% higher.

What’s the cheapest month to fly from Gulfport to Chicago?

•November is the cheapest month to fly from Gulfport to Chicago at $248 round-trip.
•April ($920) and December ($604) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 270% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

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Key details for Gulfport to Chicago flights

Low season

March

Cheapest flight

$170
Beat the crowds with an average 42% drop in travelers.
The most popular month to fly with an average 60% increase in travelers.
One-way flight from Gulfport to Chicago Midway 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 answers about this route, including flight times, airports, airlines and booking tips.

  • 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

  • How long is a flight from Gulfport to Chicago?

    A nonstop flight from Gulfport to Chicago takes 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.

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

    Round-trip flights from Gulfport to Chicago range from $315 to $587, with an average of $391 over the past 12 months. Anything below $315 counts as a good deal.

  • 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 $255 to $1,720. That means the highest observed fare was about 7x 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 $185, which is 40% below the typical average for this route.

  • 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 averaging $64:

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

    Near Chicago Midway Airport (MDW) — daily rates averaging $84:

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

    Near Chicago Greater Rockford Airport (RFD) — daily rates averaging $81:

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

  • 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).

  • 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) - 44% of one-stop connections
    • Charlotte Douglas (CLT) - 32% of one-stop connections
    • Dallas/Fort Worth (DFW) - 14% of one-stop connections
    • Houston George Bush Intcntl (IAH) - 10% of one-stop connections

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

    Yes. Flexible dates can save you up to 68% on flights from Gulfport to Chicago. 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.

  • 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 10m, compared with 5h 48m via Charlotte Douglas (CLT) and 6h 06m via Dallas/Fort Worth (DFW).

  • What popular places can I visit in Chicago?

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

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 are flexible, aim for a Tuesday departure and avoid flying on Sunday. On this route, Tuesday flights average $299, about $621 less than Sunday fares (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 $672 less than the most expensive month, which is April (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 Chicago Midway Airport

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