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$229+ Cheap flights from Gainesville (GNV) to Chicago (CHI)

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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
GNV — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Gainesville to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Gainesville (GNV) to Chicago (CHI). 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 September 11, 2025.

Round-trip from

$329
(Delta)

One-way from

$229
(Delta)

Popular in

October

Cheapest in

August

Average price

$412
From Gainesville Regional to Chicago (CHI)
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One-way flight from Gainesville Regional to Chicago (CHI)
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Highest demand for flights based on searches. 7% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Gainesville to Chicago

Cheapest flights from Gainesville to Chicago
Explore the most affordable flight options available from Gainesville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Delta deal was found by Cheapflights users on 9/10. 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 10/111:26 pmGNV - ORD
1 stop6h 23mDelta
Sat 10/186:45 amORD - GNV
1 stop4h 56mDelta
Deal found 9/10$329
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/83:02 pmGNV - ORD
1 stop7h 08mAmerican Airlines
Wed 10/157:10 amORD - GNV
1 stop6h 09mAmerican Airlines
Deal found 9/10$362
This American Airlines deal was found by Cheapflights users on 9/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/297:11 amGNV - ORD
1 stop8h 55mAmerican Airlines
Thu 11/65:00 amORD - GNV
1 stop4h 50mAmerican Airlines
Deal found 9/9$368
This American Airlines deal was found by Cheapflights users on 9/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/134:43 pmGNV - ORD
1 stop7h 29mAmerican Airlines
Sat 9/204:40 pmORD - GNV
1 stop6h 19mAmerican Airlines
Deal found 9/9$395
This Delta deal was found by Cheapflights users on 9/10. 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 11/267:04 pmGNV - MDW
1 stop5h 28mDelta
Mon 12/15:34 pmMDW - GNV
1 stop4h 37mDelta
Deal found 9/10$403
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/76:45 pmGNV - ORD
1 stop5h 52mAmerican Airlines
Mon 11/108:20 amORD - GNV
1 stop6h 15mAmerican Airlines
Deal found 9/10$407
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/119:18 amGNV - ORD
1 stop7h 47mAmerican Airlines
Sat 10/188:11 amORD - GNV
2 stops7h 10mAmerican Airlines
Deal found 9/10$423
This Delta deal was found by Cheapflights users on 9/10. 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 11/76:35 pmGNV - MDW
1 stop4h 39mDelta
Mon 11/105:34 pmMDW - GNV
1 stop4h 37mDelta
Deal found 9/10$437
This American Airlines deal was found by Cheapflights users on 9/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/137:44 pmGNV - ORD
1 stop5h 09mAmerican Airlines
Wed 10/158:35 amORD - GNV
1 stop4h 44mAmerican Airlines
Deal found 9/11$452
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/25:00 amGNV - ORD
1 stop6h 06mAmerican Airlines
Mon 11/36:46 amORD - GNV
1 stop4h 44mAmerican Airlines
Deal found 9/10$457
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/254:24 pmGNV - ORD
1 stop8h 28mAmerican Airlines
Mon 9/294:40 pmORD - GNV
1 stop6h 19mAmerican Airlines
Deal found 9/10$467
This Delta deal was found by Cheapflights users on 9/9. 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 9/287:06 pmGNV - ORD
1 stop5h 48mDelta
Wed 10/15:30 amORD - GNV
1 stop6h 01mDelta
Deal found 9/9$520

Cheapflights Fare Finder

 
Customize your flight search to find flights from Gainesville to Chicago 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 September 11, 2025.
Use the filters below to find and compare flights from Gainesville to Chicago that are best for you.

Fly from

Gainesville

Fly to

Chicago

Route

Depart

Return

Price

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Sat 10/11

1:26 pm-6:49 pm

1 stop6h 23m

Chicago O'Hare Intl

Sat 10/18

6:45 am-12:41 pm

1 stop4h 56m

$329

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Wed 10/8

3:02 pm-9:10 pm

1 stop7h 08m

Chicago O'Hare Intl

Wed 10/15

7:10 am-2:19 pm

1 stop6h 09m

$362

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Wed 10/8

3:02 pm-9:10 pm

1 stop7h 08m

Chicago O'Hare Intl

Wed 10/22

8:35 am-2:19 pm

1 stop4h 44m

$362

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Wed 11/26

1:37 pm-6:47 pm

1 stop6h 10m

Chicago O'Hare Intl

Mon 12/1

5:32 am-12:52 pm

1 stop6h 20m

$368

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Wed 11/26

7:04 pm-11:32 pm

1 stop5h 28m

Chicago Midway

Mon 12/1

5:34 pm-11:11 pm

1 stop4h 37m

$403

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Fri 11/7

4:15 pm-9:21 pm

1 stop6h 06m

Chicago O'Hare Intl

Mon 11/10

2:50 pm-11:59 pm

1 stop8h 09m

$407

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Fri 11/7

6:35 pm-10:14 pm

1 stop4h 39m

Chicago Midway

Mon 11/10

6:00 am-12:52 pm

1 stop5h 52m

$437

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Mon 10/13

7:44 pm-11:53 pm

1 stop5h 09m

Chicago O'Hare Intl

Wed 10/15

8:35 am-2:19 pm

1 stop4h 44m

$452

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Sun 11/2

5:00 am-10:06 am

1 stop6h 06m

Chicago O'Hare Intl

Mon 11/3

6:46 am-12:30 pm

1 stop4h 44m

$457

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Fri 3/6

12:11 pm-3:41 pm

1 stop4h 30m

Chicago O'Hare Intl

Sun 3/8

8:05 am-2:41 pm

1 stop5h 36m

$487

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 31 results
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Best time to book a flight from Gainesville to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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

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

Currently, August is the cheapest month in which you can book a flight from Gainesville to Chicago (average of $245). Flying from Gainesville to Chicago in March is currently the most expensive (average of $321). 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.

What is the cheapest time of day to fly from GNV to CHI?

Find hourly flight availability from Gainesville to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

One of the essential ways to save on airfare from Gainesville to Chicago is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 10% on airfare.

What is the cheapest day to fly from Gainesville to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Gainesville to Chicago. Price data was last updated on September 8, 2024.

Travelers seeking maximum savings on their Gainesville to Chicago flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 11, 2025.
Read reviews from past customers who have flown Delta and American Airlines from Gainesville to Chicago. 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
8.0
Very good
7,960 reviews

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.9

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
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.9

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.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.9

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 Chicago. 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?

    For a flight from Gainesville to Chicago, you will be flying from Gainesville Regional. Gainesville Regional (GNV) is just 4.2 mi from the center of the city. Gainesville Regional is the only Gainesville airport and it handles 0 outbound flights to Chicago per day. 2 airlines have flights to Chicago from Gainesville Regional on a regular basis.

  • How long is the flight from Gainesville to Chicago?

    There are many flights that can get you from Gainesville to Chicago in 6h 23m. Fly via Delta or American Airlines to get the fastest option. The distance from Gainesville to Chicago is about 905 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Gainesville to Chicago round-trip?

    American Airlines, at $301, was found to be the cheapest airline from Gainesville to Chicago. An alternate airline flying to your destination would be Delta. American Airlines is 41% cheaper than the average price of flights available within the next 90 days to this destination.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Gainesville to Chicago 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?

    Currently, August is the cheapest month in which you can book a flight from Gainesville to Chicago (average of $245). Flying from Gainesville to Chicago in March is currently the most expensive (average of $321). 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?

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

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Top 2 airlines flying from Gainesville to Chicago

Discover the top 2 airlines that operate flights from Gainesville to Chicago. 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$301Average$492FlexibilityNo cancel feeOn-time71%
DeltaCheapest$302Average$488FlexibilityNo cancel feeOn-timeN/A

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