$277 Cheap Flights from Gainesville (GNV) to Chicago (MDW)

View $277 flight on Wed, Jun 17, 2026Opens in a new window

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

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Cheap Flights from Gainesville to Chicago (GNV-MDW)

Prices were available within the past 7 days and start at $277 for one-way flights and $399 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Jun 17 - Tue, Jun 23
GNV
Gainesville
MDW
Chicago
$399 Roundtrip, found 9 hours ago
$399
Roundtrip
found 9 hours ago
Select Delta flight, departing Wed, Jun 17 from Gainesville to Chicago, returning Tue, Jun 23, priced at $399 found 9 hours ago
Delta
Wed, Jun 17 - Tue, Jun 23
GNV
Gainesville
MDW
Chicago
$422 Roundtrip, found 9 hours ago
$422
Roundtrip
found 9 hours ago
Select Delta flight, departing Wed, Jun 17 from Gainesville to Chicago, returning Tue, Jun 23, priced at $422 found 9 hours ago
Delta
Wed, Jul 22 - Mon, Aug 3
GNV
Gainesville
MDW
Chicago
$423 Roundtrip, found 4 days ago
$423
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Jul 22 from Gainesville to Chicago, returning Mon, Aug 3, priced at $423 found 4 days ago
Delta
Fri, Jul 3 - Wed, Jul 8
GNV
Gainesville
MDW
Chicago
$442 Roundtrip, found 5 days ago
$442
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Jul 3 from Gainesville to Chicago, returning Wed, Jul 8, priced at $442 found 5 days ago
Delta
Wed, Jun 17 - Tue, Jun 23
GNV
Gainesville
MDW
Chicago
$445 Roundtrip, found 9 hours ago
$445
Roundtrip
found 9 hours ago
Select Delta flight, departing Wed, Jun 17 from Gainesville to Chicago, returning Tue, Jun 23, priced at $445 found 9 hours ago
Delta
Thu, Aug 6 - Mon, Aug 10
GNV
Gainesville
MDW
Chicago
$447 Roundtrip, found 2 days ago
$447
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Aug 6 from Gainesville to Chicago, returning Mon, Aug 10, priced at $447 found 2 days ago
Delta
Wed, Jun 17 - Tue, Jun 23
GNV
Gainesville
MDW
Chicago
$449 Roundtrip, found 9 hours ago
$449
Roundtrip
found 9 hours ago
Select Delta flight, departing Wed, Jun 17 from Gainesville to Chicago, returning Tue, Jun 23, priced at $449 found 9 hours ago
Delta
Fri, May 29 - Mon, Jun 1
GNV
Gainesville
MDW
Chicago
$454 Roundtrip, found 2 days ago
$454
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, May 29 from Gainesville to Chicago, returning Mon, Jun 1, priced at $454 found 2 days ago
Delta
Wed, May 20 - Sat, May 23
GNV
Gainesville
MDW
Chicago
$455 Roundtrip, found 1 day ago
$455
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, May 20 from Gainesville to Chicago, returning Sat, May 23, priced at $455 found 1 day ago
Delta
Sat, May 9 - Sat, May 16
GNV
Gainesville
MDW
Chicago
$463 Roundtrip, found 9 hours ago
$463
Roundtrip
found 9 hours ago
Select Delta flight, departing Sat, May 9 from Gainesville to Chicago, returning Sat, May 16, priced at $463 found 9 hours ago

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 $455
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $455

Frequently asked questions

How much does a flight from Gainesville, FL (GNV-Gainesville Regional) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights and cheap return flights from $399 Gainesville, FL (GNV-Gainesville Regional) to Chicago, IL (MDW-Midway Intl.) with Expedia. One-way flights usually range from $308 to $555, and return flights typically cost between $364 and $934. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Gainesville, FL (GNV-Gainesville Regional) to Chicago, IL (MDW-Midway Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Gainesville, FL (GNV-Gainesville Regional) to Chicago, IL (MDW-Midway Intl.)?
The cheapest month to fly from GNV to MDW is June when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Gainesville, FL (GNV-Gainesville Regional) to Chicago, IL (MDW-Midway Intl.)?
Enter GNV to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Gainesville, FL (GNV-Gainesville Regional) to Chicago, IL (MDW-Midway Intl.)?
Delta is one of the cheapest airlines offering connecting flights from Gainesville, FL (GNV) to Chicago, IL (MDW) starting from around $679 with a layover in Hartsfield-Jackson Atlanta Intl. (ATL) for a round-trip ticket. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Gainesville, FL (GNV-Gainesville Regional) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Gainesville, FL (GNV-Gainesville Regional) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Gainesville, FL (GNV-Gainesville Regional) to Chicago, IL (MDW-Midway Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Gainesville, FL (GNV-Gainesville Regional) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Gainesville Regional Airport (GNV) to Chicago Midway International Airport (MDW) typically departs at around 6:00 AM local time, operated by Delta Airlines. This seasonal service is available in December, allowing you to maximize your time in Chicago. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Gainesville, FL (GNV-Gainesville Regional) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Gainesville, FL (GNV) to Chicago, IL (MDW) are in the early morning, from 6am to 9am. About 44% of passengers prefer this time window. Delta Air Lines operates flights during this time. This timing works well for travelers looking to make the most of their day in Chicago.
How long does it take to fly from Gainesville, FL (GNV-Gainesville Regional) to Chicago, IL (MDW-Midway Intl.)?
Flying from GNV to MDW with a connection usually takes about 7 hours, traveling roughly 890 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Gainesville, FL (GNV-Gainesville Regional) to Chicago, IL (MDW-Midway Intl.)?
First class seats are offered on the GNV to MDW route with Delta Air Lines.
How do I earn miles on a Gainesville, FL (GNV-Gainesville Regional) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Gainesville, FL (GNV-Gainesville Regional) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Gainesville Regional (GNV)?
When traveling from Gainesville Regional (GNV) to Chicago, you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW). Some flights may connect through major hubs like Hartsfield-Jackson Atlanta Intl. (ATL), Charlotte-Douglas Intl. (CLT), Miami Intl. (MIA) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Gainesville, FL (GNV-Gainesville Regional) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Gainesville, FL (GNV-Gainesville Regional) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Gainesville, FL (GNV-Gainesville Regional) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Gainesville, FL (GNV-Gainesville Regional) to Chicago, IL (MDW-Midway Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Gainesville, FL (GNV-Gainesville Regional) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Gainesville, FL (GNV-Gainesville Regional) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Gainesville Regional
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$398
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 June. 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 2026. You can also book with separate airlines for your outbound and return journeys, from $277 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

*Flight schedules are subject to change.

*Available to One Key members.

 

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