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Cheap flights from Gainesville to Chicago from $279

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 12/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Gainesville to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
9:44 am - 4:05 pmGNV  Gainesville Regional-ORD Chicago O'Hare Intl
7h 21m1 stop Charlotte Douglas
American Airlines Logo
8:05 am - 4:01 pmORD  Chicago O'Hare Intl-GNV Gainesville Regional
6h 56m1 stop Charlotte Douglas
$409American Airlines
Sat, Oct 24 - Sat, Nov 7
American Airlines Logo
1:49 pm - 5:51 pmGNV  Gainesville Regional-ORD Chicago O'Hare Intl
5h 02m1 stop Charlotte Douglas
American Airlines Logo
1:17 pm - 6:52 pmORD  Chicago O'Hare Intl-GNV Gainesville Regional
4h 35m1 stop Charlotte Douglas
$409American Airlines
Wed, Oct 21 - Sat, Oct 24
Delta Logo
5:00 pm - 10:44 pmGNV  Gainesville Regional-MDW Chicago Midway
6h 44m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 12:39 pmMDW  Chicago Midway-GNV Gainesville Regional
5h 34m1 stop Atlanta Hartsfield-Jackson
$409Delta
Sat, Sep 26 - Sat, Oct 3
Delta Logo
6:03 am - 11:50 amGNV  Gainesville Regional-MDW Chicago Midway
6h 47m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:04 am - 12:48 pmMDW  Chicago Midway-GNV Gainesville Regional
5h 44m1 stop Atlanta Hartsfield-Jackson
$409Delta
Wed, Oct 21 - Sat, Oct 24
Delta Logo
5:35 pm - 10:36 pmGNV  Gainesville Regional-MDW Chicago Midway
6h 01m1 stop Atlanta Hartsfield-Jackson
Delta Logo
10:56 am - 6:16 pmMDW  Chicago Midway-GNV Gainesville Regional
6h 20m1 stop Atlanta Hartsfield-Jackson
$409Delta
Sat, Sep 5 - Sun, Sep 6
Delta Logo
6:00 am - 10:10 amGNV  Gainesville Regional-MDW Chicago Midway
5h 10m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 12:39 pmMDW  Chicago Midway-GNV Gainesville Regional
5h 34m1 stop Atlanta Hartsfield-Jackson
$409Delta
Sun, Sep 6 - Wed, Sep 9
Delta Logo
10:19 am - 4:19 pmGNV  Gainesville Regional-MDW Chicago Midway
7h 00m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:04 am - 12:48 pmMDW  Chicago Midway-GNV Gainesville Regional
5h 44m1 stop Atlanta Hartsfield-Jackson
$409Delta
Tue, Oct 13 - Tue, Oct 20
Delta Logo
10:19 am - 3:17 pmGNV  Gainesville Regional-MDW Chicago Midway
5h 58m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:04 am - 12:48 pmMDW  Chicago Midway-GNV Gainesville Regional
5h 44m1 stop Atlanta Hartsfield-Jackson
$409Delta
Sat, Oct 17 - Tue, Oct 20
Delta Logo
5:00 pm - 10:44 pmGNV  Gainesville Regional-MDW Chicago Midway
6h 44m1 stop Atlanta Hartsfield-Jackson
Delta Logo
11:35 am - 6:11 pmMDW  Chicago Midway-GNV Gainesville Regional
5h 36m1 stop Atlanta Hartsfield-Jackson
$409Delta
Wed, Sep 9 - Fri, Sep 11
Delta Logo
6:57 pm - 10:44 pmGNV  Gainesville Regional-MDW Chicago Midway
4h 47m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 12:39 pmMDW  Chicago Midway-GNV Gainesville Regional
5h 34m1 stop Atlanta Hartsfield-Jackson
$409Delta
Fri, Sep 11 - Wed, Sep 16

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American Airlines flights from Gainesville to Chicago

Our best American Airlines deals on Gainesville to Chicago flight tickets
American Airlines
Oct 24
GNV9:44 amGainesville Regional
7h 21m
1 stop
ORD4:05 pmChicago O'Hare Intl
Nov 7
ORD8:05 amChicago O'Hare Intl
6h 56m
1 stop
GNV4:01 pmGainesville Regional
$409
American Airlines
Sep 1
GNV5:45 amGainesville Regional
6h 06m
1 stop
ORD10:51 amChicago O'Hare Intl
Sep 5
ORD5:05 amChicago O'Hare Intl
7h 23m
1 stop
GNV1:28 pmGainesville Regional
$441
American Airlines
Sep 5
GNV5:45 amGainesville Regional
7h 30m
1 stop
ORD12:15 pmChicago O'Hare Intl
Sep 6
ORD6:49 amChicago O'Hare Intl
5h 39m
1 stop
GNV1:28 pmGainesville Regional
$465

Delta flights from Gainesville to Chicago

Our best Delta deals on Gainesville to Chicago flight tickets
Delta
Sep 11
GNV6:57 pmGainesville Regional
4h 47m
1 stop
MDW10:44 pmChicago Midway
Sep 16
MDW6:05 amChicago Midway
5h 34m
1 stop
GNV12:39 pmGainesville Regional
$409
Delta
Oct 12
GNV7:03 pmGainesville Regional
15h 22m
1 stop
ORD9:25 amChicago O'Hare Intl
Oct 17
ORD5:27 amChicago O'Hare Intl
6h 21m
1 stop
GNV12:48 pmGainesville Regional
$424
Delta
Dec 13
GNV7:06 pmGainesville Regional
14h 35m
1 stop
ORD8:41 amChicago O'Hare Intl
Jan 13
ORD11:10 amChicago O'Hare Intl
3h 54m
1 stop
GNV4:04 pmGainesville Regional
$427

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 August 8, 2026.
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

Cheapest round-trip

GainesvilleChicago

GNV Gainesville Regional - ORD Chicago O'Hare Intl

GNVORD

Gainesville Regional

Sat 10/24

9:44 am-4:05 pm

1 stop7h 21m

Chicago O'Hare Intl

Sat 11/7

8:05 am-4:01 pm

1 stop6h 56m

$409
Quickest round-trip

GainesvilleChicago

GNV Gainesville Regional - ORD Chicago O'Hare Intl

GNVORD

Gainesville Regional

Wed 10/21

1:49 pm-5:51 pm

1 stop5h 02m

Chicago O'Hare Intl

Sat 10/24

1:17 pm-6:52 pm

1 stop4h 35m

$409

GainesvilleChicago

GNV Gainesville Regional - MDW Chicago Midway

GNVMDW

Gainesville Regional

Sat 9/26

5:00 pm-10:44 pm

1 stop6h 44m

Chicago Midway

Sat 10/3

6:05 am-12:39 pm

1 stop5h 34m

$409

GainesvilleChicago

GNV Gainesville Regional - MDW Chicago Midway

GNVMDW

Gainesville Regional

Wed 10/21

6:03 am-11:50 am

1 stop6h 47m

Chicago Midway

Sat 10/24

6:04 am-12:48 pm

1 stop5h 44m

$409

GainesvilleChicago

GNV Gainesville Regional - MDW Chicago Midway

GNVMDW

Gainesville Regional

Sat 9/5

5:35 pm-10:36 pm

1 stop6h 01m

Chicago Midway

Sun 9/6

10:56 am-6:16 pm

1 stop6h 20m

$409

GainesvilleChicago

GNV Gainesville Regional - MDW Chicago Midway

GNVMDW

Gainesville Regional

Sun 9/6

6:00 am-10:10 am

1 stop5h 10m

Chicago Midway

Wed 9/9

6:05 am-12:39 pm

1 stop5h 34m

$409

GainesvilleChicago

GNV Gainesville Regional - MDW Chicago Midway

GNVMDW

Gainesville Regional

Tue 10/13

10:19 am-4:19 pm

1 stop7h 00m

Chicago Midway

Tue 10/20

6:04 am-12:48 pm

1 stop5h 44m

$409

GainesvilleChicago

GNV Gainesville Regional - MDW Chicago Midway

GNVMDW

Gainesville Regional

Sat 10/17

10:19 am-3:17 pm

1 stop5h 58m

Chicago Midway

Tue 10/20

6:04 am-12:48 pm

1 stop5h 44m

$409

GainesvilleChicago

GNV Gainesville Regional - MDW Chicago Midway

GNVMDW

Gainesville Regional

Wed 9/9

5:00 pm-10:44 pm

1 stop6h 44m

Chicago Midway

Fri 9/11

11:35 am-6:11 pm

1 stop5h 36m

$409

GainesvilleChicago

GNV Gainesville Regional - MDW Chicago Midway

GNVMDW

Gainesville Regional

Fri 9/11

6:57 pm-10:44 pm

1 stop4h 47m

Chicago Midway

Wed 9/16

6:05 am-12:39 pm

1 stop5h 34m

$409

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 month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Gainesville, with most prices found around $402. If you’re not able to fly to Chicago in September, then February is your next best option. Flight prices from Gainesville to Chicago during February average around $407.

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 07m

Direct flights

None
The fastest flight from Gainesville to Chicago takes 4h 07m
There are no direct flights from Gainesville to Chicago. There are no popular flight routes from Gainesville to Chicago.
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Frequently asked questions about flying from Gainesville to Chicago

  • 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 07m.

  • 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 $361Free CancellationRating
7.1
11,889 reviews
Search American Airlines flights

Traveling to a place near Chicago?

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