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Midway

$268+ Cheap flights from Gainesville (GNV) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/30. Fares are subject to change and may not be available on all flights or dates of travel.
GNV — MDW
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap flight deals from Gainesville to Midway

Cheapest flights from Gainesville to Midway
Explore the most affordable flight options available from Gainesville to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2026.

This Delta deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:00 am
GNV
-
MDW
1 stop5h 21m
Delta
Mon 2/2310:49 am
MDW
-
GNV
1 stop6h 24m
Delta
Deal found 1/20$368
This Delta deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:00 pm
GNV
-
MDW
1 stop4h 31m
Delta
Sat 4/186:30 am
MDW
-
GNV
1 stop5h 37m
Delta
Deal found 1/21$394
This Delta deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/207:00 pm
GNV
-
MDW
1 stop4h 31m
Delta
Mon 2/2312:45 pm
MDW
-
GNV
1 stop4h 28m
Delta
Deal found 1/20$407
This Delta deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/84:59 pm
GNV
-
MDW
1 stop5h 46m
Delta
Sun 5/106:00 am
MDW
-
GNV
1 stop5h 23m
Delta
Deal found 1/20$433
This Delta deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/56:00 am
GNV
-
MDW
1 stop4h 53m
Delta
Sat 2/76:25 am
MDW
-
GNV
1 stop5h 01m
Delta
Deal found 1/19$461
This Delta deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/116:00 am
GNV
-
MDW
1 stop6h 59m
Delta
Sun 2/156:00 am
MDW
-
GNV
1 stop5h 26m
Delta
Deal found 1/19$493
This Delta deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/2410:10 am
GNV
-
MDW
1 stop6h 28m
Delta
Sun 1/256:00 am
MDW
-
GNV
1 stop5h 26m
Delta
Deal found 1/20$497
This Delta deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/44:59 pm
GNV
-
MDW
1 stop6h 23m
Delta
Sun 2/86:00 am
MDW
-
GNV
1 stop5h 26m
Delta
Deal found 1/20$507
This Delta deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/234:59 pm
GNV
-
MDW
1 stop6h 23m
Delta
Sun 1/256:00 am
MDW
-
GNV
1 stop5h 26m
Delta
Deal found 1/20$559
This Delta deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:00 am
GNV
-
MDW
1 stop6h 59m
Delta
Fri 3/610:49 am
MDW
-
GNV
1 stop4h 13m
Delta
Deal found 1/20$615
This Delta deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/137:00 pm
GNV
-
MDW
1 stop4h 31m
Delta
Sun 3/156:00 am
MDW
-
GNV
1 stop5h 47m
Delta
Deal found 1/19$687

Find flight deals from Gainesville to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Gainesville (GNV) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$368
(Delta)

One-way from

$268
(Delta)

Popular in

November

Cheapest in

August

Average price

$559
Provider with most accurate pricing for Gainesville Regional-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Gainesville Regional-Chicago Midway flights.
Search Deals
From Gainesville Regional to Chicago Midway
Search Deals
One-way flight from Gainesville Regional to Chicago Midway
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Gainesville to Midway 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, Cheapflights users made 2,558,603 searches. Data last updated January 21, 2026.
Use the filters below to find and compare flights from Gainesville to Chicago Midway Airport that are best for you.

Fly from

Gainesville

Fly to

Midway

Route

Depart

Return

Price

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Sat 2/21

6:00 am-10:21 am

1 stop5h 21m

Chicago Midway

Mon 2/23

10:49 am-6:13 pm

1 stop6h 24m

$368

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Sun 4/12

7:00 pm-10:31 pm

1 stop4h 31m

Chicago Midway

Sat 4/18

6:30 am-1:07 pm

1 stop5h 37m

$394

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Fri 2/20

4:59 pm-10:31 pm

1 stop6h 32m

Chicago Midway

Sun 2/22

6:00 am-12:26 pm

1 stop5h 26m

$407

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Fri 3/6

1:15 pm-5:45 pm

1 stop5h 30m

Chicago Midway

Sun 3/8

6:00 am-12:47 pm

1 stop5h 47m

$407

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Fri 2/20

7:00 pm-10:31 pm

1 stop4h 31m

Chicago Midway

Mon 2/23

12:45 pm-6:13 pm

1 stop4h 28m

$407

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Thu 2/12

4:59 pm-10:31 pm

1 stop6h 32m

Chicago Midway

Sun 2/15

6:00 am-12:26 pm

1 stop5h 26m

$453

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Fri 5/8

4:59 pm-9:45 pm

1 stop5h 46m

Chicago Midway

Sun 5/10

6:00 am-12:23 pm

1 stop5h 23m

$459

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Wed 2/11

6:00 am-11:59 am

1 stop6h 59m

Chicago Midway

Sun 2/15

6:00 am-12:26 pm

1 stop5h 26m

$493

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Wed 2/4

4:59 pm-10:22 pm

1 stop6h 23m

Chicago Midway

Sun 2/8

6:00 am-12:26 pm

1 stop5h 26m

$507

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Thu 3/5

6:00 am-11:59 am

1 stop6h 59m

Chicago Midway

Fri 3/6

10:49 am-4:02 pm

1 stop4h 13m

$615

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 20 results
1
2
  • Most accurate provider: When it comes to deals on Gainesville-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Gainesville-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Gainesville-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Gainesville-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Gainesville-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Gainesville to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Gainesville with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Gainesville to Chicago Midway Airport

What is the cheapest month to book a flight from Gainesville to Chicago Midway Airport?

Currently, January is the cheapest month in which you can book a flight from Gainesville to Chicago Midway Airport (average of $58). Flying from Gainesville to Chicago Midway Airport in March is currently the most expensive (average of $172). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated January 21, 2026.
Read reviews from past customers who have flown Delta from Gainesville to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,089 reviews

Entertainment

7.8

Food

7.2

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
7.9
Good
8,089 reviews
Delta
7.9
Good
8,089 reviews

Entertainment

7.8

Food

7.2

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

Related info for your journey

Find useful and relevant information for your journey from Gainesville to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Gainesville to Chicago Midway?

    Most people fly from Gainesville Regional (GNV) if they book a flight from Gainesville to Chicago Midway. On average, Gainesville Regional has 0 outbound flights to Chicago Midway per day from 1 airline. Gainesville Regional is conveniently located just 4.2 mi from Gainesville’s city center.

  • How long is the flight from Gainesville to Chicago Midway Airport?

    For as low as $368, Delta can have you in Chicago Midway Airport from Gainesville in 5h 21m. The distance from Gainesville to Chicago Midway Airport is about 889 mi.

  • What is the cheapest airline to fly from Gainesville to Chicago Midway Airport round-trip?

    Cheapflights users have booked flights from Gainesville to Chicago Midway Airport round-trip from $213.

  • Can I find deals for flights from Gainesville to Midway that include hotel bookings?

    Yes. In addition to deals on Gainesville to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Gainesville to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Gainesville to Midway.

  • Can I find deals for business class flights from Gainesville to Midway?

    Yes. Cheapflights offers flight deals from Gainesville to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Gainesville to Chicago Midway Airport?

    Currently, January is the cheapest month in which you can book a flight from Gainesville to Chicago Midway Airport (average of $58). Flying from Gainesville to Chicago Midway Airport in March is currently the most expensive (average of $172). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Top airline flying from Gainesville to Midway

Discover the top airline that operate flights from Gainesville to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$213Average$436FlexibilityNo cancel feeOn-timeN/A

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