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Cheap flights from Gainesville to Chicago from $333

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 9/16. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Gainesville to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
10:19 am - 4:19 pmGNV  Gainesville Regional-MDW Chicago Midway
7h 00m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:04 am - 12:48 pmMDW  Chicago Midway-GNV Gainesville Regional
5h 44m1 stop Atlanta Hartsfield-Jackson
$409Delta
Tue, Oct 13 - Tue, Oct 20
Delta Logo
7:03 pm - 10:03 amGNV  Gainesville Regional-MDW Chicago Midway
16h 00m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:04 am - 12:48 pmMDW  Chicago Midway-GNV Gainesville Regional
5h 44m1 stop Atlanta Hartsfield-Jackson
$424Delta
Mon, Oct 12 - Tue, Oct 20
Delta Logo
10:19 am - 4:19 pmGNV  Gainesville Regional-MDW Chicago Midway
7h 00m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:15 pm - 9:34 amMDW  Chicago Midway-GNV Gainesville Regional
15h 19m1 stop Atlanta Hartsfield-Jackson
$427Delta
Tue, Oct 13 - Mon, Oct 19
Delta Logo
7:03 pm - 10:33 pmGNV  Gainesville Regional-MDW Chicago Midway
4h 30m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:04 am - 12:48 pmMDW  Chicago Midway-GNV Gainesville Regional
5h 44m1 stop Atlanta Hartsfield-Jackson
$433Delta
Fri, Oct 16 - Tue, Oct 20
Delta Logo
7:03 pm - 10:03 amGNV  Gainesville Regional-MDW Chicago Midway
16h 00m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:19 pm - 9:34 amMDW  Chicago Midway-GNV Gainesville Regional
16h 15m1 stop Atlanta Hartsfield-Jackson
$439Delta
Mon, Oct 12 - Sat, Oct 17
Delta Logo
7:03 pm - 10:03 amGNV  Gainesville Regional-MDW Chicago Midway
16h 00m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:15 pm - 9:34 amMDW  Chicago Midway-GNV Gainesville Regional
15h 19m1 stop Atlanta Hartsfield-Jackson
$442Delta
Mon, Oct 12 - Mon, Oct 19
Delta Logo
6:57 pm - 10:44 pmGNV  Gainesville Regional-MDW Chicago Midway
4h 47m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 12:39 pmMDW  Chicago Midway-GNV Gainesville Regional
5h 34m1 stop Atlanta Hartsfield-Jackson
$443Delta
Tue, Sep 29 - Sat, Oct 3
Delta Logo
6:03 am - 11:50 amGNV  Gainesville Regional-MDW Chicago Midway
6h 47m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:19 pm - 9:34 amMDW  Chicago Midway-GNV Gainesville Regional
16h 15m1 stop Atlanta Hartsfield-Jackson
$448Delta
Thu, Oct 15 - Sat, Oct 17
Delta Logo
6:03 am - 11:50 amGNV  Gainesville Regional-MDW Chicago Midway
6h 47m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:15 pm - 9:34 amMDW  Chicago Midway-GNV Gainesville Regional
15h 19m1 stop Atlanta Hartsfield-Jackson
$451Delta
Thu, Oct 15 - Mon, Oct 19
Delta Logo
7:01 pm - 10:36 pmGNV  Gainesville Regional-MDW Chicago Midway
4h 35m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 12:39 pmMDW  Chicago Midway-GNV Gainesville Regional
5h 34m1 stop Atlanta Hartsfield-Jackson
$457Delta
Thu, Sep 3 - Thu, Sep 10

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Delta flights from Gainesville to Chicago Midway Airport

Our best Delta deals on Gainesville to Chicago Midway Airport flight tickets
Delta
Oct 13
GNV10:19 amGainesville Regional
7h 00m
1 stop
MDW4:19 pmChicago Midway
Oct 20
MDW6:04 amChicago Midway
5h 44m
1 stop
GNV12:48 pmGainesville Regional
$409
Delta
Oct 12
GNV7:03 pmGainesville Regional
16h 00m
1 stop
MDW10:03 amChicago Midway
Oct 20
MDW6:04 amChicago Midway
5h 44m
1 stop
GNV12:48 pmGainesville Regional
$424
Delta
Oct 13
GNV10:19 amGainesville Regional
7h 00m
1 stop
MDW4:19 pmChicago Midway
Oct 19
MDW5:15 pmChicago Midway
15h 19m
1 stop
GNV9:34 amGainesville Regional
$427

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 August 9, 2026.
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

Cheapest round-trip

GainesvilleChicago

GNV Gainesville Regional - MDW Chicago Midway

GNVMDW

Gainesville Regional

Tue 10/13

10:19 am-4:19 pm

1 stop7h 00m

Chicago Midway

Tue 10/20

6:04 am-12:48 pm

1 stop5h 44m

$409

GainesvilleChicago

GNV Gainesville Regional - MDW Chicago Midway

GNVMDW

Gainesville Regional

Mon 10/12

7:03 pm-10:03 am

1 stop16h 00m

Chicago Midway

Tue 10/20

6:04 am-12:48 pm

1 stop5h 44m

$424

GainesvilleChicago

GNV Gainesville Regional - MDW Chicago Midway

GNVMDW

Gainesville Regional

Tue 10/13

10:19 am-4:19 pm

1 stop7h 00m

Chicago Midway

Mon 10/19

5:15 pm-9:34 am

1 stop15h 19m

$427

GainesvilleChicago

GNV Gainesville Regional - MDW Chicago Midway

GNVMDW

Gainesville Regional

Fri 10/16

7:03 pm-10:33 pm

1 stop4h 30m

Chicago Midway

Tue 10/20

6:04 am-12:48 pm

1 stop5h 44m

$433

GainesvilleChicago

GNV Gainesville Regional - MDW Chicago Midway

GNVMDW

Gainesville Regional

Mon 10/12

7:03 pm-10:03 am

1 stop16h 00m

Chicago Midway

Sat 10/17

4:19 pm-9:34 am

1 stop16h 15m

$439

GainesvilleChicago

GNV Gainesville Regional - MDW Chicago Midway

GNVMDW

Gainesville Regional

Mon 10/12

7:03 pm-10:03 am

1 stop16h 00m

Chicago Midway

Mon 10/19

5:15 pm-9:34 am

1 stop15h 19m

$442

GainesvilleChicago

GNV Gainesville Regional - MDW Chicago Midway

GNVMDW

Gainesville Regional

Tue 9/29

6:57 pm-10:44 pm

1 stop4h 47m

Chicago Midway

Sat 10/3

6:05 am-12:39 pm

1 stop5h 34m

$443

GainesvilleChicago

GNV Gainesville Regional - MDW Chicago Midway

GNVMDW

Gainesville Regional

Thu 10/15

6:03 am-11:50 am

1 stop6h 47m

Chicago Midway

Sat 10/17

4:19 pm-9:34 am

1 stop16h 15m

$448

GainesvilleChicago

GNV Gainesville Regional - MDW Chicago Midway

GNVMDW

Gainesville Regional

Thu 10/15

6:03 am-11:50 am

1 stop6h 47m

Chicago Midway

Mon 10/19

5:15 pm-9:34 am

1 stop15h 19m

$451
Quickest round-trip

GainesvilleChicago

GNV Gainesville Regional - MDW Chicago Midway

GNVMDW

Gainesville Regional

Thu 9/3

7:01 pm-10:36 pm

1 stop4h 35m

Chicago Midway

Thu 9/10

6:05 am-12:39 pm

1 stop5h 34m

$457

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 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 55% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 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

Fastest flight time

4h 07m

Direct flights

None
The fastest flight from Gainesville to Chicago Midway Airport takes 4h 07m
There are no direct flights from Gainesville to Chicago Midway Airport. There are no popular flight routes from Gainesville to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Gainesville to Chicago Midway Airport

  • 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 07m.

  • 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 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.

Traveling to a place near Chicago?

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