$297 Cheap Flights from Gainesville (GNV) to Chicago (MDW)

View $297 flight on Wed, Dec 10, 2025Opens in a new window

Popular airlines from Gainesville Regional Airport (GNV) to Chicago Midway Airport (MDW)

Cheap Flights from Gainesville to Chicago (GNV-MDW)

Prices were available within the past 7 days and start at $297 for one-way flights and $329 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Mar 14 - Tue, Mar 17
GNV
Gainesville
MDW
Chicago
$329 Roundtrip, found 2 days ago
$329
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Mar 14 from Gainesville to Chicago, returning Tue, Mar 17, priced at $329 found 2 days ago
Delta
Sat, Dec 13 - Tue, Jan 13
GNV
Gainesville
MDW
Chicago
$364 Roundtrip, found 1 day ago
$364
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Dec 13 from Gainesville to Chicago, returning Tue, Jan 13, priced at $364 found 1 day ago
Delta
Tue, Dec 30 - Fri, Jan 2
GNV
Gainesville
MDW
Chicago
$368 Roundtrip, found 20 hours ago
$368
Roundtrip
found 20 hours ago
Select Delta flight, departing Tue, Dec 30 from Gainesville to Chicago, returning Fri, Jan 2, priced at $368 found 20 hours ago
Delta
Wed, Nov 12 - Mon, Nov 24
GNV
Gainesville
MDW
Chicago
$382 Roundtrip, found 3 days ago
$382
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Nov 12 from Gainesville to Chicago, returning Mon, Nov 24, priced at $382 found 3 days ago
Delta
Thu, Nov 27 - Mon, Dec 1
GNV
Gainesville
MDW
Chicago
$394 Roundtrip, just found
$394
Roundtrip
just found
Select Delta flight, departing Thu, Nov 27 from Gainesville to Chicago, returning Mon, Dec 1, priced at $394 just found
Delta
Sat, Dec 13 - Tue, Jan 13
GNV
Gainesville
MDW
Chicago
$399 Roundtrip, found 1 day ago
$399
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Dec 13 from Gainesville to Chicago, returning Tue, Jan 13, priced at $399 found 1 day ago
Delta
Sat, Dec 6 - Sun, Dec 7
GNV
Gainesville
MDW
Chicago
$403 Roundtrip, found 2 days ago
$403
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Dec 6 from Gainesville to Chicago, returning Sun, Dec 7, priced at $403 found 2 days ago
Delta
Sat, Mar 14 - Sun, Mar 15
GNV
Gainesville
MDW
Chicago
$404 Roundtrip, found 2 days ago
$404
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Mar 14 from Gainesville to Chicago, returning Sun, Mar 15, priced at $404 found 2 days ago
Delta
Thu, Nov 20 - Wed, Dec 3
GNV
Gainesville
MDW
Chicago
$408 Roundtrip, found 3 days ago
$408
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Nov 20 from Gainesville to Chicago, returning Wed, Dec 3, priced at $408 found 3 days ago
Delta
Wed, Nov 12 - Sun, Nov 23
GNV
Gainesville
MDW
Chicago
$421 Roundtrip, found 3 days ago
$421
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Nov 12 from Gainesville to Chicago, returning Sun, Nov 23, priced at $421 found 3 days ago

Find the cheapest month to fly from Gainesville (GNV) to Chicago (MDW)

August is typically the cheapest month to fly

From $286 - $574 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $374
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $374

Frequently asked questions

How much does a flight from Gainesville Regional Airport (GNV) to Midway Intl. Airport (MDW) cost?
Lock in a cheap one-way flight from $297 or cheap return flight from $329 from Gainesville Regional Airport (GNV) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Gainesville Regional Airport (GNV) to Midway Intl. Airport (MDW)?
The cheapest month to fly from GNV to MDW is March, when there's less demand. Off-peak season is usually when you'll find lower airfares between these airports.
What is the cheapest airline that flies from Gainesville Regional Airport (GNV) to Midway Intl. Airport (MDW)?
Use the filter tool on Expedia to compare airlines and find the most affordable carrier that'll fly you from GNV to MDW. Then, sort your results by "Price (lowest to highest)" to pick up the best deal available.
How many flights per day from Gainesville Regional Airport (GNV) to Midway Intl. Airport (MDW)?
You'll have to book a flight with a layover when traveling from Gainesville Regional Airport (GNV) to Midway Intl. Airport (MDW). There are no daily direct flights on this route. However, simply filter your search to include one or more stops to find the best option for your trip.
What day of the week has the most flights from GNV to MDW?
Friday is generally the busiest day for flights, while Tuesday is often the quietest.* Just remember that flight schedules can change based on a number of factors, including the time of year and carrier.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Gainesville Regional Airport (GNV) to Midway Intl. Airport (MDW)?
To reach Midway Intl. Airport (MDW) without delays, book a flight that leaves from Gainesville Regional Airport (GNV) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Gainesville Regional Airport (GNV) to Midway Intl. Airport (MDW) last-minute?
Booking your ticket from GNV to MDW shortly before your trip is usually more expensive. However, if you're flexible with your departure dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a GNV to MDW flight and hotel package?
You'll generally save money by booking a GNV to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one convenient place. Once you've chosen your ideal flights and accommodations, you can add extras such as car rentals, tours and activities.
Can I cancel or change the date of my flight from Gainesville Regional Airport (GNV) to Midway Intl. Airport (MDW)?
In most instances, you can cancel or reschedule your GNV to MDW flight. However, additional fees may apply, especially if you made your booking more than 24 hours ago. Check your itinerary for the airline's policies and fees on flight changes, or if you need further details, head to our Customer Service portal.

Travel information

Origin airport
Gainesville Regional
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$328
Distance
890 mi

Book with confidence

Gainesville to Chicago Flights

The cheapest times to fly from Gainesville to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Gainesville to Chicago are during the month of March. You can find some of the cheapest flights from Gainesville to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Gainesville to Chicago

Sunday is one of the best days to book for cheap flights from Gainesville to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Gainesville to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Gainesville to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $297 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Gainesville to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Gainesville to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Gainesville to Chicago Flights

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*Available to One Key members.