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Cheap flights from Gainesville to Chicago from $297

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Gainesville to Chicago departing on 1/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Gainesville to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 10:06 amGNV-MDW
5h 06m1 stop
Delta Logo
6:00 am - 12:26 pmMDW-GNV
5h 26m1 stop
$329Delta
Find Deal
Sat, Feb 14 - Wed, Feb 18
Delta Logo
10:13 am - 2:10 pmGNV-ORD
4h 57m1 stop
Delta Logo
6:45 am - 12:26 pmORD-GNV
4h 41m1 stop
$329Delta
Find Deal
Sat, Feb 14 - Wed, Feb 18
American Airlines Logo
6:35 am - 2:01 pmGNV-ORD
8h 26m2 stops
American Airlines Logo
1:54 pm - 7:22 pmORD-GNV
4h 28m1 stop
$334American Airlines
Find Deal
Wed, Feb 11 - Sat, Feb 14
Delta Logo
6:00 am - 10:07 amGNV-ORD
5h 07m1 stop
Delta Logo
7:00 am - 10:40 pmORD-GNV
14h 40m2 stops
$360Delta
Find Deal
Sat, Feb 14 - Wed, Feb 18
Delta Logo
6:00 am - 11:58 amGNV-MDW
6h 58m1 stop
Delta Logo
6:00 am - 11:20 amMDW-GNV
4h 20m1 stop
$368Delta
Find Deal
Mon, Dec 29 - Thu, Jan 1
Delta Logo
7:00 pm - 11:57 pmGNV-ORD
5h 57m1 stop
Delta Logo
5:25 am - 12:26 pmORD-GNV
6h 01m1 stop
$368Delta
Find Deal
Thu, Feb 12 - Sun, Feb 15
Delta Logo
6:00 am - 10:07 amGNV-ORD
5h 07m1 stop
Delta Logo
7:00 am - 10:40 pmORD-GNV
14h 40m2 stops
$376Delta
Find Deal
Sat, Feb 14 - Wed, Feb 18
Delta Logo
10:13 am - 11:03 amGNV-MDW
25h 50m2 stops
Delta Logo
6:00 am - 12:26 pmMDW-GNV
5h 26m1 stop
$381Delta
Find Deal
Sat, Feb 14 - Wed, Feb 18
Delta Logo
5:30 pm - 9:41 amGNV-ORD
17h 11m2 stops
Delta Logo
5:25 am - 12:26 pmORD-GNV
6h 01m1 stop
$381Delta
Find Deal
Sat, Feb 14 - Wed, Feb 18
American Airlines Logo
7:47 pm - 11:53 pmGNV-ORD
5h 06m1 stop
American Airlines Logo
4:05 pm - 10:36 pmORD-GNV
5h 31m1 stop
$407American Airlines
Find Deal
Fri, Feb 13 - Sun, Feb 15

American Airlines flights from Gainesville to Chicago

Our best American Airlines deals on Gainesville to Chicago flight tickets
American Airlines
Feb 11
GNV6:35 amGainesville Regional
8h 26m
2 stops
ORD2:01 pmChicago O'Hare Intl
Feb 14
ORD1:54 pmChicago O'Hare Intl
4h 28m
1 stop
GNV7:22 pmGainesville Regional
$334
Find similar
American Airlines
Feb 13
GNV7:47 pmGainesville Regional
5h 06m
1 stop
ORD11:53 pmChicago O'Hare Intl
Feb 15
ORD4:05 pmChicago O'Hare Intl
5h 31m
1 stop
GNV10:36 pmGainesville Regional
$407
Find similar
American Airlines
Dec 8
GNV6:00 amGainesville Regional
6h 07m
1 stop
ORD11:07 amChicago O'Hare Intl
Jan 7
ORD3:48 pmChicago O'Hare Intl
6h 42m
2 stops
GNV11:30 pmGainesville Regional
$413
Find similar

Delta flights from Gainesville to Chicago

Our best Delta deals on Gainesville to Chicago flight tickets
Delta
Feb 14
GNV10:13 amGainesville Regional
4h 57m
1 stop
ORD2:10 pmChicago O'Hare Intl
Feb 18
ORD6:45 amChicago O'Hare Intl
4h 41m
1 stop
GNV12:26 pmGainesville Regional
$329
Find similar
Delta
Feb 14
GNV6:00 amGainesville Regional
5h 07m
1 stop
ORD10:07 amChicago O'Hare Intl
Feb 18
ORD7:00 amChicago O'Hare Intl
14h 40m
2 stops
GNV10:40 pmGainesville Regional
$360
Find similar
Delta
Feb 12
GNV7:00 pmGainesville Regional
5h 57m
1 stop
ORD11:57 pmChicago O'Hare Intl
Feb 15
ORD5:25 amChicago O'Hare Intl
6h 01m
1 stop
GNV12:26 pmGainesville Regional
$368
Find similar

momondo 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, momondo users made 832,500 searches. Data last updated November 26, 2025.
Use the filters below to find and compare flights from Gainesville to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Sat 2/14

6:00 am-10:06 am

1 stop5h 06m

Chicago Midway

Wed 2/18

6:00 am-12:26 pm

1 stop5h 26m

$329

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Sat 2/14

10:13 am-2:10 pm

1 stop4h 57m

Chicago O'Hare Intl

Wed 2/18

6:45 am-12:26 pm

1 stop4h 41m

$329

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Wed 2/11

6:35 am-2:01 pm

2 stops8h 26m

Chicago O'Hare Intl

Sat 2/14

1:54 pm-7:22 pm

1 stop4h 28m

$334

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Sat 2/14

6:00 am-10:07 am

1 stop5h 07m

Chicago O'Hare Intl

Wed 2/18

7:00 am-10:40 pm

2 stops14h 40m

$360

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Mon 12/29

6:00 am-11:58 am

1 stop6h 58m

Chicago Midway

Thu 1/1

6:00 am-11:20 am

1 stop4h 20m

$368

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Thu 2/12

7:00 pm-11:57 pm

1 stop5h 57m

Chicago O'Hare Intl

Sun 2/15

5:25 am-12:26 pm

1 stop6h 01m

$368

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Sat 2/14

6:00 am-10:07 am

1 stop5h 07m

Chicago O'Hare Intl

Wed 2/18

7:00 am-10:40 pm

2 stops14h 40m

$376

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Sat 2/14

10:13 am-11:03 am

2 stops25h 50m

Chicago Midway

Wed 2/18

6:00 am-12:26 pm

1 stop5h 26m

$381

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Sat 2/14

5:30 pm-9:41 am

2 stops17h 11m

Chicago O'Hare Intl

Wed 2/18

5:25 am-12:26 pm

1 stop6h 01m

$381

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Fri 2/13

7:47 pm-11:53 pm

1 stop5h 06m

Chicago O'Hare Intl

Sun 2/15

4:05 pm-10:36 pm

1 stop5h 31m

$407

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Gainesville to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $322. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Gainesville to Chicago for around $864.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Gainesville to Chicago during this time can be as low as $462. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $510.

Can stopping save me money on Gainesville to Chicago flights?

You could potentially save up to 33% on your flight if you consider stops on a Gainesville to Chicago flight.

When to book flights from Gainesville to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Gainesville to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Gainesville to Chicago (GNV to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Gainesville to Chicago

Fastest flight time

4h 21m

Direct flights

None
The fastest flight from Gainesville to Chicago takes 4h 21m
There are no direct flights from Gainesville to Chicago. There are no popular flight routes from Gainesville to Chicago.
Search flight deals

  • How far is Gainesville Regional to Chicago by plane?

    There are 894.3 mi between Gainesville Regional and Chicago. In terms of flight time, this usually takes a little over 4h 27m.

  • When did momondo last update prices for flights from Gainesville Regional Airport to Chicago?

    Prices for flights from Gainesville Regional Airport to Chicago are refreshed on a daily basis.

  • How many operators does momondo search for flights from Gainesville Regional Airport to Chicago?

  • How old do you have to be to fly from Gainesville Regional Airport to Chicago?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Gainesville Regional Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular airline from Gainesville to Chicago?

Best airlines flying from Gainesville to Chicago

Compare and see reviews for airlines that fly from Gainesville to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $301Free CancellationRating
7.2
11,038 reviews
Search American Airlines flights
DeltaPriceFrom $302Free CancellationRating
7.9
7,998 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Gainesville to Chicago?

Finding the right flight to Chicago from Gainesville is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Gainesville to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Gainesville with this policy.

How can momondo help me find flights from Gainesville to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Gainesville. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Gainesville to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Gainesville. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport