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Cheap flights from Gainesville to Chicago from $309

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Gainesville to Chicago departing on 12/21. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Gainesville to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 9:54 amGNV-MDW
4h 54m1 stop
Delta Logo
12:50 pm - 6:19 pmMDW-GNV
4h 29m1 stop
$368Delta
Find Deal
Sat, Dec 13 - Tue, Dec 16
Delta Logo
10:10 am - 3:44 pmGNV-MDW
6h 34m1 stop
Delta Logo
11:21 am - 5:38 pmMDW-GNV
5h 17m1 stop
$407Delta
Find Deal
Sat, Dec 6 - Mon, Jan 12
Delta Logo
7:04 pm - 11:47 pmGNV-MDW
5h 43m1 stop
Delta Logo
4:29 pm - 10:42 pmMDW-GNV
5h 13m1 stop
$435Delta
Find Deal
Tue, Dec 2 - Sat, Dec 6
Delta Logo
6:55 pm - 10:22 pmGNV-MDW
4h 27m1 stop
Delta Logo
6:00 am - 1:32 pmMDW-GNV
6h 32m1 stop
$444Delta
Find Deal
Sat, Dec 20 - Wed, Dec 24
Delta Logo
6:00 am - 9:54 amGNV-MDW
4h 54m1 stop
Delta Logo
11:21 am - 5:38 pmMDW-GNV
5h 17m1 stop
$447Delta
Find Deal
Sat, Dec 6 - Mon, Jan 12
Delta Logo
6:00 am - 6:06 pmGNV-MDW
13h 06m2 stops
Delta Logo
5:39 pm - 10:42 pmMDW-GNV
4h 03m1 stop
$473Delta
Find Deal
Sat, Dec 13 - Tue, Dec 16
Delta Logo
6:00 am - 9:54 amGNV-MDW
4h 54m1 stop
Delta Logo
1:14 pm - 2:56 pmMDW-GNV
24h 42m2 stops
$477Delta
Find Deal
Sat, Dec 13 - Tue, Dec 16
Delta Logo
7:04 pm - 11:47 pmGNV-MDW
5h 43m1 stop
Delta Logo
6:00 am - 12:58 pmMDW-GNV
5h 58m1 stop
$487Delta
Find Deal
Thu, Dec 4 - Mon, Dec 8
Delta Logo
6:00 am - 9:54 amGNV-MDW
4h 54m1 stop
Delta Logo
6:40 pm - 2:56 pmMDW-GNV
19h 16m2 stops
$495Delta
Find Deal
Sat, Dec 13 - Tue, Dec 16
Delta Logo
1:15 pm - 5:45 pmGNV-MDW
5h 30m1 stop
Delta Logo
10:53 am - 6:15 pmMDW-GNV
6h 22m1 stop
$568Delta
Find Deal
Tue, Feb 17 - Sun, Feb 22

Delta flights from Gainesville to Chicago Midway Airport

Our best Delta deals on Gainesville to Chicago Midway Airport flight tickets
Delta
Dec 13
GNV6:00 amGainesville Regional
4h 54m
1 stop
MDW9:54 amChicago Midway
Dec 16
MDW12:50 pmChicago Midway
4h 29m
1 stop
GNV6:19 pmGainesville Regional
$368
Find similar
Delta
Dec 6
GNV10:10 amGainesville Regional
6h 34m
1 stop
MDW3:44 pmChicago Midway
Jan 12
MDW11:21 amChicago Midway
5h 17m
1 stop
GNV5:38 pmGainesville Regional
$407
Find similar
Delta
Dec 2
GNV7:04 pmGainesville Regional
5h 43m
1 stop
MDW11:47 pmChicago Midway
Dec 6
MDW4:29 pmChicago Midway
5h 13m
1 stop
GNV10:42 pmGainesville Regional
$435
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Gainesville to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated November 19, 2025.
Use the filters below to find and compare flights from Gainesville to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Sat 12/13

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

Tue 12/16

12:50 pm-6:19 pm

1 stop4h 29m

$368

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Sat 12/6

10:10 am-3:44 pm

1 stop6h 34m

Chicago Midway

Mon 1/12

11:21 am-5:38 pm

1 stop5h 17m

$407

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Tue 12/2

7:04 pm-11:47 pm

1 stop5h 43m

Chicago Midway

Sat 12/6

4:29 pm-10:42 pm

1 stop5h 13m

$435

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Sat 12/20

6:55 pm-10:22 pm

1 stop4h 27m

Chicago Midway

Wed 12/24

6:00 am-1:32 pm

1 stop6h 32m

$444

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Sat 12/6

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

Mon 1/12

11:21 am-5:38 pm

1 stop5h 17m

$447

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Sat 12/13

6:00 am-6:06 pm

2 stops13h 06m

Chicago Midway

Tue 12/16

5:39 pm-10:42 pm

1 stop4h 03m

$473

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Sat 12/13

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

Tue 12/16

1:14 pm-2:56 pm

2 stops24h 42m

$477

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Thu 12/4

7:04 pm-11:47 pm

1 stop5h 43m

Chicago Midway

Mon 12/8

6:00 am-12:58 pm

1 stop5h 58m

$487

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Sat 12/13

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

Tue 12/16

6:40 pm-2:56 pm

2 stops19h 16m

$495

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Tue 2/17

1:15 pm-5:45 pm

1 stop5h 30m

Chicago Midway

Sun 2/22

10:53 am-6:15 pm

1 stop6h 22m

$568

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Gainesville to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Gainesville Regional to Chicago Midway?

Delta is the most popular carrier operating from Gainesville Regional to Chicago Midway

What airlines fly to Chicago Midway Airport?

Southwest, Frontier and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Gainesville according to our data. Southwest is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 4 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

When to book flights from Gainesville to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Gainesville to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Gainesville to Chicago Midway Airport (GNV to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Gainesville to Chicago Midway Airport

Direct flights

None
There are no direct flights from Gainesville to Chicago Midway Airport. There are no popular flight routes from Gainesville to Chicago Midway Airport.
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  • How far is Gainesville Regional to Chicago Midway by plane?

    Chicago Midway is 890.8 mi away from Gainesville Regional. A reasonable flight in good conditions will take 4h 54m.

  • When did momondo last update prices for flights from Gainesville Regional Airport to Chicago Midway Airport?

    Prices for flights from Gainesville Regional Airport to Chicago Midway Airport were last updated today.

  • How many operators does momondo search for flights from Gainesville Regional Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Gainesville Regional Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Gainesville Regional Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular airline from Gainesville to Chicago Midway Airport?

Best airlines flying from Gainesville to Chicago Midway Airport

Compare and see reviews for airlines that fly from Gainesville to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $356Free CancellationRating
7.9
8,004 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Gainesville to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Gainesville.

Can I find flights from Gainesville to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Gainesville to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Gainesville to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Gainesville to Chicago.

I’m not ready to book a flight from Gainesville to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Gainesville. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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