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Cheap flights from Chicago to Gainesville from $165

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Gainesville departing on 10/21. 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 Chicago to Gainesville

Cheap round-trip flights

Delta Logo
6:00 am - 12:41 pmMDW-GNV
5h 41m1 stop
Delta Logo
5:57 pm - 10:14 pmGNV-MDW
5h 17m1 stop
$329Delta
Find Deal
Sat, Oct 18 - Sat, Oct 25
American Airlines Logo
12:15 pm - 7:47 pmORD-GNV
6h 32m1 stop
American Airlines Logo
7:00 am - 2:25 pmGNV-ORD
8h 25m1 stop
$329American Airlines
Find Deal
Sat, Dec 13 - Sat, Jan 10
American Airlines Logo
6:00 am - 3:53 pmORD-GNV
8h 53m1 stop
American Airlines Logo
4:24 pm - 9:45 pmGNV-ORD
6h 21m1 stop
$362American Airlines
Find Deal
Fri, Sep 5 - Tue, Sep 9
American Airlines Logo
1:22 pm - 10:28 pmORD-GNV
8h 06m1 stop
American Airlines Logo
7:16 am - 12:36 pmGNV-ORD
6h 20m1 stop
$387American Airlines
Find Deal
Fri, Oct 24 - Sun, Oct 26
American Airlines Logo
6:00 am - 3:54 pmORD-GNV
8h 54m1 stop
American Airlines Logo
4:24 pm - 11:17 pmGNV-ORD
7h 53m1 stop
$417American Airlines
Find Deal
Sun, Sep 7 - Sun, Sep 14
Delta Logo
5:40 am - 11:33 amORD-GNV
4h 53m1 stop
Delta Logo
10:10 am - 4:18 pmGNV-ORD
7h 08m1 stop
$432Delta
Find Deal
Sat, Dec 27 - Fri, Jan 2
American Airlines Logo
8:11 am - 4:21 pmORD-GNV
7h 10m2 stops
American Airlines Logo
4:46 pm - 9:29 pmGNV-ORD
5h 43m1 stop
$445American Airlines
Find Deal
Sat, Oct 18 - Sat, Oct 25
Delta Logo
11:15 am - 5:50 pmORD-GNV
5h 35m1 stop
Delta Logo
6:35 pm - 10:37 pmGNV-ORD
5h 02m1 stop
$447Delta
Find Deal
Thu, Sep 4 - Mon, Sep 8
American Airlines Logo
1:37 pm - 11:13 pmORD-GNV
8h 36m2 stops
American Airlines Logo
4:43 pm - 11:12 pmGNV-ORD
7h 29m1 stop
$452American Airlines
Find Deal
Thu, Sep 4 - Mon, Sep 8
American Airlines Logo
7:10 am - 1:16 pmORD-GNV
5h 06m1 stop
American Airlines Logo
4:46 pm - 9:24 pmGNV-ORD
5h 38m1 stop
$453American Airlines
Find Deal
Thu, Oct 16 - Thu, Oct 23

American Airlines flights from Chicago to Gainesville

Our best American Airlines deals on Chicago to Gainesville flight tickets
American Airlines
Dec 13
ORD12:15 pmChicago O'Hare Intl
6h 32m
1 stop
GNV7:47 pmGainesville Regional
Jan 10
GNV7:00 amGainesville Regional
8h 25m
1 stop
ORD2:25 pmChicago O'Hare Intl
$329
Find similar
American Airlines
Sep 5
ORD6:00 amChicago O'Hare Intl
8h 53m
1 stop
GNV3:53 pmGainesville Regional
Sep 9
GNV4:24 pmGainesville Regional
6h 21m
1 stop
ORD9:45 pmChicago O'Hare Intl
$362
Find similar
American Airlines
Oct 24
ORD1:22 pmChicago O'Hare Intl
8h 06m
1 stop
GNV10:28 pmGainesville Regional
Oct 26
GNV7:16 amGainesville Regional
6h 20m
1 stop
ORD12:36 pmChicago O'Hare Intl
$387
Find similar

Delta flights from Chicago to Gainesville

Our best Delta deals on Chicago to Gainesville flight tickets
Delta
Oct 18
MDW6:00 amChicago Midway
5h 41m
1 stop
GNV12:41 pmGainesville Regional
Oct 25
GNV5:57 pmGainesville Regional
5h 17m
1 stop
MDW10:14 pmChicago Midway
$329
Find similar
Delta
Dec 27
ORD5:40 amChicago O'Hare Intl
4h 53m
1 stop
GNV11:33 amGainesville Regional
Jan 2
GNV10:10 amGainesville Regional
7h 08m
1 stop
ORD4:18 pmChicago O'Hare Intl
$432
Find similar
Delta
Sep 4
ORD11:15 amChicago O'Hare Intl
5h 35m
1 stop
GNV5:50 pmGainesville Regional
Sep 8
GNV6:35 pmGainesville Regional
5h 02m
1 stop
ORD10:37 pmChicago O'Hare Intl
$447
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Gainesville 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 August 21, 2025.
Use the filters below to find and compare flights from Chicago to Gainesville that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoGainesville

MDW - GNV

MDWGNV

Chicago Midway

Sat 10/18

6:00 am-12:41 pm

1 stop5h 41m

Gainesville Regional

Sat 10/25

5:57 pm-10:14 pm

1 stop5h 17m

$329

ChicagoGainesville

ORD - GNV

ORDGNV

Chicago O'Hare Intl

Sat 12/13

12:15 pm-7:47 pm

1 stop6h 32m

Gainesville Regional

Sat 1/10

7:00 am-2:25 pm

1 stop8h 25m

$329

ChicagoGainesville

ORD - GNV

ORDGNV

Chicago O'Hare Intl

Fri 9/5

6:00 am-3:53 pm

1 stop8h 53m

Gainesville Regional

Tue 9/9

4:24 pm-9:45 pm

1 stop6h 21m

$362

ChicagoGainesville

ORD - GNV

ORDGNV

Chicago O'Hare Intl

Fri 10/24

1:22 pm-10:28 pm

1 stop8h 06m

Gainesville Regional

Sun 10/26

7:16 am-12:36 pm

1 stop6h 20m

$387

ChicagoGainesville

ORD - GNV

ORDGNV

Chicago O'Hare Intl

Sun 9/7

6:00 am-3:54 pm

1 stop8h 54m

Gainesville Regional

Sun 9/14

4:24 pm-11:17 pm

1 stop7h 53m

$417

ChicagoGainesville

ORD - GNV

ORDGNV

Chicago O'Hare Intl

Sat 12/27

5:40 am-11:33 am

1 stop4h 53m

Gainesville Regional

Fri 1/2

10:10 am-4:18 pm

1 stop7h 08m

$432

ChicagoGainesville

ORD - GNV

ORDGNV

Chicago O'Hare Intl

Sat 10/18

8:11 am-4:21 pm

2 stops7h 10m

Gainesville Regional

Sat 10/25

4:46 pm-9:29 pm

1 stop5h 43m

$445

ChicagoGainesville

ORD - GNV

ORDGNV

Chicago O'Hare Intl

Thu 9/4

11:15 am-5:50 pm

1 stop5h 35m

Gainesville Regional

Mon 9/8

6:35 pm-10:37 pm

1 stop5h 02m

$447

ChicagoGainesville

ORD - GNV

ORDGNV

Chicago O'Hare Intl

Thu 9/4

1:37 pm-11:13 pm

2 stops8h 36m

Gainesville Regional

Mon 9/8

4:43 pm-11:12 pm

1 stop7h 29m

$452

ChicagoGainesville

ORD - GNV

ORDGNV

Chicago O'Hare Intl

Thu 10/16

7:10 am-1:16 pm

1 stop5h 06m

Gainesville Regional

Thu 10/23

4:46 pm-9:24 pm

1 stop5h 38m

$453

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 Gainesville from

How to get the cheapest flight ticket from Chicago to Gainesville

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 typical price of a round-trip flight between Chicago and Gainesville?

What is the cheapest month to fly to Gainesville?

The month of June is, on average, the cheapest month to fly to Gainesville from Chicago, with most prices found around $408. If you’re not able to fly to Gainesville in June, then May is your next best option. Flight prices from Chicago to Gainesville during May average around $426.

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

The cheapest day to depart on your flight to Gainesville is on a Saturday when prices can be found for as low as $338. This is often the case because there is less demand to fly during this day of the week. Flights from Chicago to Gainesville on a Thursday will generally be more expensive and average around $563. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

In the afternoon is the cheapest time of day to fly from Chicago to Gainesville when you can find flight prices for as low as $479. Flying to Gainesville in the afternoon is an ideal time because this is during off-peak travel hours. Flights to Gainesville are more costly in the evening, with an average ticket price of $692. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

How have Chicago to Gainesville flight prices changed over time?

As of August 2025, prices for Chicago to Gainesville flights are approximately 12% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Gainesville

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

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

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

Direct flights

None
There are no direct flights from Chicago to Gainesville. There are no popular flight routes from Chicago to Gainesville.
Search flight deals

  • How far is Chicago to Gainesville Regional by plane?

    Chicago and Gainesville Regional are 894.3 mi apart from one another. 3h 42m is a normal flight duration for this route.

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

    Prices for flights from Chicago to Gainesville Regional Airport are updated daily.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Gainesville Regional Airport.

  • What documentation or ID do you need to fly to Gainesville Regional Airport?

    The required travel and health documents for your Gainesville Regional Airport 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 Gainesville Regional Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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

Best airlines flying from Chicago to Gainesville

Compare and see reviews for airlines that fly from Chicago to Gainesville with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $328Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $328Free CancellationRating
7.9
7,981 reviews
Search Delta flights

Traveling to a place near Gainesville?

Book flights to Gainesville if you plan to visit one of these locations
Lake City
Alachua
Trenton

Why use momondo?

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

It is quick and easy to find Chicago to Gainesville flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Gainesville that suits you.

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

momondo does allow users to show only those flights to Gainesville from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

momondo helps you find the best flight between Chicago and Gainesville by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are simply researching potential flights to Gainesville, momondo offers a useful price alert feature which will track prices for flights to Gainesville from Chicago and alert you when they change.

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