HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$297+ 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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
GNV — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Gainesville to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 30, 2025.

This Delta deal was found by Cheapflights users on 10/30. 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 12/66:00 amGNV - MDW
1 stop4h 54mDelta
Sat 12/134:29 pmMDW - GNV
1 stop5h 13mDelta
Deal found 10/30$329
This American Airlines deal was found by Cheapflights users on 10/30. 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 12/66:00 amGNV - ORD
1 stop6h 07mAmerican Airlines
Sat 12/138:20 amORD - GNV
1 stop5h 49mAmerican Airlines
Deal found 10/30$329
This Delta deal was found by Cheapflights users on 10/28. 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 12/66:00 amGNV - MDW
1 stop4h 54mDelta
Mon 1/125:31 pmMDW - GNV
1 stop4h 11mDelta
Deal found 10/28$368
This Delta deal was found by Cheapflights users on 10/30. 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 12/61:43 pmGNV - ORD
1 stop6h 00mDelta
Mon 1/122:49 pmORD - GNV
1 stop6h 53mDelta
Deal found 10/30$368
This American Airlines deal was found by Cheapflights users on 10/30. 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 12/66:30 amGNV - ORD
2 stops7h 38mAmerican Airlines
Mon 1/129:11 amORD - GNV
1 stop5h 46mAmerican Airlines
Deal found 10/30$373
This Delta deal was found by Cheapflights users on 10/29. 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 11/207:04 pmGNV - MDW
1 stop5h 36mDelta
Mon 11/246:00 amMDW - GNV
1 stop5h 52mDelta
Deal found 10/29$388
This Delta deal was found by Cheapflights users on 10/28. 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 12/127:04 pmGNV - MDW
1 stop5h 43mDelta
Mon 12/156:00 amMDW - GNV
1 stop5h 58mDelta
Deal found 10/28$407
This Delta deal was found by Cheapflights users on 10/29. 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 12/127:04 pmGNV - ORD
1 stop5h 57mDelta
Mon 12/156:45 amORD - GNV
1 stop7h 11mDelta
Deal found 10/29$407
This American Airlines deal was found by Cheapflights users on 10/30. 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 12/66:30 amGNV - ORD
1 stop5h 33mAmerican Airlines
Sat 1/106:05 amORD - GNV
1 stop5h 25mAmerican Airlines
Deal found 10/30$411
This Delta deal was found by Cheapflights users on 10/29. 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.
Tue 11/111:37 pmGNV - ORD
1 stop4h 09mDelta
Wed 11/195:23 amORD - GNV
1 stop6h 29mDelta
Deal found 10/29$421
This Delta deal was found by Cheapflights users on 10/29. 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 11/126:00 amGNV - MDW
1 stop6h 52mDelta
Sat 11/156:00 amMDW - GNV
1 stop5h 52mDelta
Deal found 10/29$435
This Delta deal was found by Cheapflights users on 10/29. 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 11/121:37 pmGNV - ORD
1 stop6h 14mDelta
Sat 11/156:45 amORD - GNV
1 stop5h 07mDelta
Deal found 10/29$435

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$329
(Delta)

One-way from

$297
(Delta)

Popular in

October

Cheapest in

August

Average price

$944
Provider with most accurate pricing for Gainesville Regional-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Gainesville Regional-Chicago (CHI) flights.
Search Deals
From Gainesville Regional to Chicago (CHI)
Search Deals
One-way flight from Gainesville Regional to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($122 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($42 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 30, 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 - MDW

GNVMDW

Gainesville Regional

Sat 12/6

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

Sat 12/13

4:29 pm-10:42 pm

1 stop5h 13m

$329

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Thu 12/4

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

Sat 12/6

4:29 pm-10:42 pm

1 stop5h 13m

$368

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Sat 12/6

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

Mon 1/12

5:31 pm-10:42 pm

1 stop4h 11m

$368

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Sat 12/6

1:43 pm-6:43 pm

1 stop6h 00m

Chicago O'Hare Intl

Mon 1/12

2:49 pm-10:42 pm

1 stop6h 53m

$368

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Sat 12/6

6:30 am-1:08 pm

2 stops7h 38m

Chicago O'Hare Intl

Mon 1/12

9:11 am-3:57 pm

1 stop5h 46m

$373

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Thu 11/20

7:04 pm-11:40 pm

1 stop5h 36m

Chicago Midway

Mon 11/24

6:00 am-12:52 pm

1 stop5h 52m

$388

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Fri 12/12

7:04 pm-11:47 pm

1 stop5h 43m

Chicago Midway

Mon 12/15

6:00 am-12:58 pm

1 stop5h 58m

$407

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Sat 11/22

4:10 pm-10:30 pm

1 stop7h 20m

Chicago O'Hare Intl

Sun 11/23

9:51 am-3:01 pm

1 stop4h 10m

$407

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Sat 12/6

6:30 am-11:03 am

1 stop5h 33m

Chicago O'Hare Intl

Sat 1/10

6:05 am-12:30 pm

1 stop5h 25m

$411

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Wed 11/12

7:04 pm-10:30 pm

1 stop4h 26m

Chicago O'Hare Intl

Wed 11/19

6:45 am-3:01 pm

1 stop7h 16m

$421

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 37 results
1
2
3
4

Compare providers for flights from Gainesville to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Gainesville to Chicago in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Gainesville-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Gainesville-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Gainesville-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Gainesville-Chicago flights, Cheapflights users trust eDreams the most. eDreams 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 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 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, November is the cheapest month in which you can book a flight from Gainesville to Chicago (average of $54). Flying from Gainesville to Chicago in June is currently the most expensive (average of $113). 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 October 30, 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 afternoon tend to be the most expensive. A flight at noon could potentially save you up to 23% 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 December 16, 2024.

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

How much does it cost to fly round-trip from Gainesville to Chicago?

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 October 30, 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
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.2

Food

7.3

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
7,998 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.2

Food

7.3

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
11,035 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

7.9

Boarding

8.2

Food

7.3

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 4h 54m. Fly via Delta or American Airlines to get the fastest option. The distance from Gainesville to Chicago is about 889 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 43% 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, November is the cheapest month in which you can book a flight from Gainesville to Chicago (average of $54). Flying from Gainesville to Chicago in June is currently the most expensive (average of $113). 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
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Gainesville to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Fort Lauderdale to O'Hare Intl flights
Tampa to O'Hare Intl flights
Miami to O'Hare Intl flights
Orlando to O'Hare Intl flights
Tampa to Midway flights
Orlando to Midway flights
Miami to Midway flights
Fort Lauderdale to Midway flights
Jacksonville to O'Hare Intl flights
Fort Myers to O'Hare Intl flights
West Palm Beach to O'Hare Intl flights
Sarasota to O'Hare Intl flights
Orlando to St. Louis flights
Fort Myers to Midway flights
Pensacola to O'Hare Intl flights
West Palm Beach to Midway flights
Jacksonville to Midway flights
Fort Lauderdale to St. Louis flights
Tampa to St. Louis flights
Miami to St. Louis flights
Jacksonville to St. Louis flights
Key West to O'Hare Intl flights
Pensacola to Midway flights
Sarasota to Midway flights
St Petersburg to Rockford flights
Panama City to O'Hare Intl flights
Valparaiso to O'Hare Intl flights
Fort Myers to St. Louis flights
Sarasota to St. Louis flights
Daytona Beach to O'Hare Intl flights
Pensacola to St. Louis flights
West Palm Beach to St. Louis flights
Orlando to Moline flights
Jacksonville to Peoria flights
Tallahassee to O'Hare Intl flights
Daytona Beach to Midway flights
Key West to Midway flights
Gainesville to O'Hare Intl flights
Panama City to St. Louis flights
Miami to Peoria flights
Melbourne to O'Hare Intl flights
Melbourne to Midway flights
Jacksonville to Moline flights
Tallahassee to Midway flights
Tallahassee to St. Louis flights
Tampa to Moline flights
Fort Lauderdale to Peoria flights
Gainesville to Midway flights
Miami to Moline flights
Daytona Beach to St. Louis flights

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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$301Average$473FlexibilityNo cancel feeOn-time71%
DeltaCheapest$356Average$456FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.