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Cheap flights from Gainesville to Chicago 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 Gainesville to Chicago departing on 10/7. 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

Delta Logo
6:00 am - 9:34 amGNV-MDW
4h 34m1 stop
Delta Logo
10:35 am - 3:16 pmMDW-GNV
3h 41m1 stop
$356Delta
Find Deal
Wed, Sep 10 - Wed, Sep 17
Delta Logo
6:00 am - 10:04 amGNV-ORD
5h 04m1 stop
Delta Logo
9:50 am - 3:16 pmORD-GNV
4h 26m1 stop
$356Delta
Find Deal
Wed, Sep 10 - Wed, Sep 17
American Airlines Logo
4:24 pm - 9:45 pmGNV-ORD
6h 21m1 stop
American Airlines Logo
2:50 pm - 11:59 pmORD-GNV
8h 09m1 stop
$358American Airlines
Find Deal
Sat, Sep 20 - Mon, Sep 22
American Airlines Logo
6:13 am - 11:32 amGNV-ORD
6h 19m1 stop
American Airlines Logo
8:10 am - 4:08 pmORD-GNV
6h 58m2 stops
$363American Airlines
Find Deal
Wed, Sep 10 - Wed, Sep 17
Delta Logo
4:01 pm - 9:36 pmGNV-MDW
6h 35m1 stop
Delta Logo
6:00 am - 12:31 pmMDW-GNV
5h 31m1 stop
$379Delta
Find Deal
Tue, Sep 16 - Thu, Sep 18
Delta Logo
7:06 pm - 10:14 pmGNV-ORD
4h 08m1 stop
Delta Logo
7:20 am - 3:16 pmORD-GNV
6h 56m1 stop
$379Delta
Find Deal
Tue, Sep 16 - Thu, Sep 18
Delta Logo
6:35 pm - 10:37 pmGNV-ORD
5h 02m1 stop
Delta Logo
7:05 am - 1:25 pmORD-GNV
5h 20m1 stop
$383Delta
Find Deal
Tue, Sep 2 - Wed, Sep 10
Delta Logo
6:00 am - 9:36 amGNV-MDW
4h 36m1 stop
Delta Logo
6:00 am - 12:31 pmMDW-GNV
5h 31m1 stop
$385Delta
Find Deal
Tue, Sep 2 - Mon, Sep 15
Delta Logo
6:35 pm - 10:37 pmGNV-ORD
5h 02m1 stop
Delta Logo
5:30 am - 12:31 pmORD-GNV
6h 01m1 stop
$385Delta
Find Deal
Tue, Sep 2 - Mon, Sep 15
Delta Logo
6:00 am - 10:05 amGNV-ORD
5h 05m1 stop
Delta Logo
11:15 am - 5:50 pmORD-GNV
5h 35m1 stop
$387Delta
Find Deal
Thu, Sep 4 - Sat, Sep 6

American Airlines flights from Gainesville to Chicago

Our best American Airlines deals on Gainesville to Chicago flight tickets
American Airlines
Sep 20
GNV4:24 pmGainesville Regional
6h 21m
1 stop
ORD9:45 pmChicago O'Hare Intl
Sep 22
ORD2:50 pmChicago O'Hare Intl
8h 09m
1 stop
GNV11:59 pmGainesville Regional
$358
Find similar
American Airlines
Sep 10
GNV6:13 amGainesville Regional
6h 19m
1 stop
ORD11:32 amChicago O'Hare Intl
Sep 17
ORD8:10 amChicago O'Hare Intl
6h 58m
2 stops
GNV4:08 pmGainesville Regional
$363
Find similar
American Airlines
Sep 2
GNV6:01 amGainesville Regional
7h 08m
2 stops
ORD12:09 pmChicago O'Hare Intl
Sep 15
ORD2:50 pmChicago O'Hare Intl
8h 09m
1 stop
GNV11:59 pmGainesville Regional
$396
Find similar

Delta flights from Gainesville to Chicago

Our best Delta deals on Gainesville to Chicago flight tickets
Delta
Sep 10
GNV6:00 amGainesville Regional
5h 04m
1 stop
ORD10:04 amChicago O'Hare Intl
Sep 17
ORD9:50 amChicago O'Hare Intl
4h 26m
1 stop
GNV3:16 pmGainesville Regional
$356
Find similar
Delta
Sep 16
GNV7:06 pmGainesville Regional
4h 08m
1 stop
ORD10:14 pmChicago O'Hare Intl
Sep 18
ORD7:20 amChicago O'Hare Intl
6h 56m
1 stop
GNV3:16 pmGainesville Regional
$379
Find similar
Delta
Sep 2
GNV6:35 pmGainesville Regional
5h 02m
1 stop
ORD10:37 pmChicago O'Hare Intl
Sep 10
ORD7:05 amChicago O'Hare Intl
5h 20m
1 stop
GNV1:25 pmGainesville Regional
$383
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 August 16, 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

Wed 9/10

6:00 am-9:34 am

1 stop4h 34m

Chicago Midway

Wed 9/17

10:35 am-3:16 pm

1 stop3h 41m

$356

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Wed 9/10

6:00 am-10:04 am

1 stop5h 04m

Chicago O'Hare Intl

Wed 9/17

9:50 am-3:16 pm

1 stop4h 26m

$356

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Sat 9/20

4:24 pm-9:45 pm

1 stop6h 21m

Chicago O'Hare Intl

Mon 9/22

2:50 pm-11:59 pm

1 stop8h 09m

$358

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Wed 9/10

6:13 am-11:32 am

1 stop6h 19m

Chicago O'Hare Intl

Wed 9/17

8:10 am-4:08 pm

2 stops6h 58m

$363

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Tue 9/16

4:01 pm-9:36 pm

1 stop6h 35m

Chicago Midway

Thu 9/18

6:00 am-12:31 pm

1 stop5h 31m

$379

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Tue 9/16

7:06 pm-10:14 pm

1 stop4h 08m

Chicago O'Hare Intl

Thu 9/18

7:20 am-3:16 pm

1 stop6h 56m

$379

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Tue 9/2

6:35 pm-10:37 pm

1 stop5h 02m

Chicago O'Hare Intl

Wed 9/10

7:05 am-1:25 pm

1 stop5h 20m

$383

GainesvilleChicago

GNV - MDW

GNVMDW

Gainesville Regional

Tue 9/2

6:00 am-9:36 am

1 stop4h 36m

Chicago Midway

Mon 9/15

6:00 am-12:31 pm

1 stop5h 31m

$385

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Tue 9/2

6:35 pm-10:37 pm

1 stop5h 02m

Chicago O'Hare Intl

Mon 9/15

5:30 am-12:31 pm

1 stop6h 01m

$385

GainesvilleChicago

GNV - ORD

GNVORD

Gainesville Regional

Thu 9/4

6:00 am-10:05 am

1 stop5h 05m

Chicago O'Hare Intl

Sat 9/6

11:15 am-5:50 pm

1 stop5h 35m

$387

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

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 2% on your flight if you consider stops on a Gainesville to Chicago flight.

How have Gainesville to Chicago flight prices changed over time?

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

Best Price Found

$165

Fastest flight time

4h 07m

Direct flights

None

Airports in Chicago

2 airports
The best one-way flight to Chicago from Gainesville in the past 72 hours is $165. The best round-trip flight deal from Gainesville to Chicago found on momondo in the last 72 hours is $356.
The fastest flight from Gainesville to Chicago takes 4h 07m
There are no direct flights from Gainesville to Chicago. Popular non-direct routes for this connection are Gainesville Regional Airport - Chicago O'Hare Intl Airport and Gainesville Regional Airport - Chicago Midway Airport.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
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  • 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 $301Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $302Free CancellationRating
8.0
7,985 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
Lansing
Portage
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