$343+ Cheap flights from Gainesville (GNV) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
GNV — CHI
Oct 22 — Oct 291
Round-trip
1 adult, Economy
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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
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Cheapest flights from Gainesville to ChicagoExplore 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 September 22, 2026.
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 September 22, 2026.
This Delta deal was found by Cheapflights users on 9/19. 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 11/36:03 am -
1 stop5h 40m
Sat 11/74:19 pm -
1 stop4h 16m
Deal found 9/19![Delta logo]()
$429
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/249:44 am -
1 stop7h 21m
Sat 11/78:05 am -
1 stop6h 56m
Deal found 9/17![American Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 9/19. 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.
Mon 11/25:00 pm -
1 stop6h 33m
Sat 11/76:04 am -
1 stop5h 44m
Deal found 9/19![Delta logo]()
$453
This American Airlines deal was found by Cheapflights users on 9/21. 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.
Wed 10/286:00 am -
1 stop6h 10m
Mon 11/29:00 am -
1 stop5h 56m
Deal found 9/21![American Airlines logo]()
$453
This American Airlines deal was found by Cheapflights users on 9/21. 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.
Thu 11/56:20 am -
1 stop5h 42m
Sat 11/711:47 am -
1 stop5h 19m
Deal found 9/21![American Airlines logo]()
$454
This Delta deal was found by Cheapflights users on 9/21. 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 10/146:03 am -
1 stop5h 00m
Wed 10/216:04 am -
1 stop5h 41m
Deal found 9/21![Delta logo]()
$461
This Delta deal was found by Cheapflights users on 9/17. 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 10/147:03 pm -
1 stop5h 54m
Wed 10/216:30 am -
1 stop5h 15m
Deal found 9/17![Delta logo]()
$461
This Delta deal was found by Cheapflights users on 9/18. 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 10/167:03 pm -
1 stop4h 30m
Tue 10/2010:59 am -
1 stop6h 15m
Deal found 9/18![Delta logo]()
$463
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Fri 10/167:34 pm -
1 stop5h 34m
Tue 10/204:31 pm -
1 stop6h 28m
Deal found 9/17![American Airlines logo]()
$463
This Delta deal was found by Cheapflights users on 9/21. 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 11/247:06 pm -
1 stop5h 48m
Mon 11/306:49 am -
1 stop7h 09m
Deal found 9/21![Delta logo]()
$473
This Delta deal was found by Cheapflights users on 9/19. 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 12/256:00 am -
1 stop4h 13m
Fri 1/16:00 am -
1 stop4h 25m
Deal found 9/19![Delta logo]()
$477
This American Airlines deal was found by Cheapflights users on 9/17. 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 12/196:07 am -
1 stop7h 15m
Fri 1/17:59 am -
1 stop4h 28m
Deal found 9/17![American Airlines logo]()
$477
Best flights from Gainesville to ChicagoDiscover carefully curated flight deals from Gainesville to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 22, 2026.
Discover carefully curated flight deals from Gainesville to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 22, 2026.
This American Airlines deal was found by Cheapflights users on 9/18. 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 10/249:44 am -
1 stop7h 21m
Sat 11/78:05 am -
1 stop6h 56m
Deal found 9/18![American Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 9/19. 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.
Mon 11/25:00 pm -
1 stop6h 33m
Sat 11/76:04 am -
1 stop5h 44m
Deal found 9/19![Delta logo]()
$453
This Delta deal was found by Cheapflights users on 9/18. 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 10/146:03 am -
1 stop5h 00m
Wed 10/216:04 am -
1 stop5h 41m
Deal found 9/18![Delta logo]()
$461
This Delta deal was found by Cheapflights users on 9/20. 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 10/167:03 pm -
1 stop4h 30m
Tue 10/2010:59 am -
1 stop6h 15m
Deal found 9/20![Delta logo]()
$463
This Delta deal was found by Cheapflights users on 9/21. 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 11/247:06 pm -
1 stop5h 48m
Mon 11/306:49 am -
1 stop7h 09m
Deal found 9/21![Delta logo]()
$473
This Delta deal was found by Cheapflights users on 9/19. 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 10/26:57 pm -
1 stop6h 02m
Tue 10/65:27 am -
1 stop6h 21m
Deal found 9/19![Delta logo]()
$570
This Delta deal was found by Cheapflights users on 9/21. 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 11/55:00 pm -
1 stop6h 33m
Sat 11/76:04 am -
1 stop5h 44m
Deal found 9/21![Delta logo]()
$574
This Delta deal was found by Cheapflights users on 9/17. 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 10/26:57 pm -
1 stop6h 02m
Sun 10/46:40 am -
1 stop4h 59m
Deal found 9/17![Delta logo]()
$578
This Delta deal was found by Cheapflights users on 9/17. 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 10/26:57 pm -
1 stop4h 47m
Sun 10/46:05 am -
1 stop5h 34m
Deal found 9/17![Delta logo]()
$698
This Delta deal was found by Cheapflights users on 9/19. 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.
Mon 11/26:03 am -
2 stops7h 56m
Sat 11/710:35 am -
1 stop4h 23m
Deal found 9/19![Delta logo]()
$821
This Delta deal was found by Cheapflights users on 9/17. 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 10/146:03 am -
2 stops7h 56m
Wed 10/215:27 am -
1 stop6h 18m
Deal found 9/17![Delta logo]()
$821
This Delta deal was found by Cheapflights users on 9/20. 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 10/1610:19 am -
2 stops9h 10m
Tue 10/205:27 am -
1 stop6h 21m
Deal found 9/20![Delta logo]()
$821
This Delta deal was found by Cheapflights users on 9/21. 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 10/284:02 pm -
1 stop5h 36m
Mon 11/211:19 am -
2 stops9h 16m
Deal found 9/21![Delta logo]()
$821
This Delta deal was found by Cheapflights users on 9/21. 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 11/56:03 am -
2 stops7h 56m
Sat 11/75:27 am -
1 stop6h 21m
Deal found 9/21![Delta logo]()
$821
Last-minute flights from Gainesville to ChicagoDiscover last-minute flight deals from Gainesville to Chicago. Data last updated September 22, 2026 and is based on user searches.
Discover last-minute flight deals from Gainesville to Chicago. Data last updated September 22, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Thu 10/16:00 am -
1 stop5h 50m
Sun 10/42:30 pm -
1 stop7h 55m
Deal found 9/17![American Airlines logo]()
$557
This Delta deal was found by Cheapflights users on 9/17. 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 10/61:33 pm -
1 stop6h 38m
Sat 10/1010:35 am -
1 stop4h 23m
Deal found 9/17![Delta logo]()
$493
This Delta deal was found by Cheapflights users on 9/21. 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 10/146:03 am -
1 stop5h 00m
Wed 10/216:04 am -
1 stop5h 41m
Deal found 9/21![Delta logo]()
$461
This Delta deal was found by Cheapflights users on 9/17. 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 10/147:03 pm -
1 stop5h 54m
Wed 10/216:30 am -
1 stop5h 15m
Deal found 9/17![Delta logo]()
$461
This Delta deal was found by Cheapflights users on 9/17. 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 10/157:03 pm -
1 stop5h 54m
Thu 10/225:27 am -
1 stop6h 21m
Deal found 9/17![Delta logo]()
$487
This Delta deal was found by Cheapflights users on 9/17. 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 10/157:03 pm -
1 stop4h 30m
Thu 10/226:04 am -
1 stop5h 44m
Deal found 9/17![Delta logo]()
$497
This American Airlines deal was found by Cheapflights users on 9/20. 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.
Thu 10/157:34 pm -
1 stop5h 34m
Sun 10/184:31 pm -
1 stop6h 28m
Deal found 9/20![American Airlines logo]()
$497
This Delta deal was found by Cheapflights users on 9/18. 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 10/167:03 pm -
1 stop4h 30m
Tue 10/2010:59 am -
1 stop6h 15m
Deal found 9/18![Delta logo]()
$463
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Fri 10/167:34 pm -
1 stop5h 34m
Tue 10/204:31 pm -
1 stop6h 28m
Deal found 9/17![American Airlines logo]()
$463
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/249:44 am -
1 stop7h 21m
Sat 11/78:05 am -
1 stop6h 56m
Deal found 9/17![American Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 9/21. 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.
Wed 10/286:00 am -
1 stop6h 10m
Mon 11/29:00 am -
1 stop5h 56m
Deal found 9/21![American Airlines logo]()
$453
This Delta deal was found by Cheapflights users on 9/21. 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 10/287:03 pm -
1 stop4h 30m
Mon 11/26:04 am -
1 stop5h 44m
Deal found 9/21![Delta logo]()
$504
One-way flights from Gainesville to ChicagoSearch for one-way flight options from Gainesville to Chicago. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
Search for one-way flight options from Gainesville to Chicago. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
This Delta deal was found by Cheapflights users on 9/21. 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 1/16:00 am -
1 stop4h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$343
This American Airlines deal was found by Cheapflights users on 9/19. 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.
Sun 11/86:00 am -
1 stop6h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![American Airlines logo]()
$343
This Delta deal was found by Cheapflights users on 9/17. 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 12/3010:10 am -
2 stops11h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$360
This American Airlines deal was found by Cheapflights users on 9/21. 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.
Sun 1/311:13 am -
1 stop6h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![American Airlines logo]()
$383
This Delta deal was found by Cheapflights users on 9/22. 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.
Sun 10/114:02 pm -
1 stop5h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Delta logo]()
$403
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Thu 12/3111:13 am -
2 stops9h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![American Airlines logo]()
$408
This Delta deal was found by Cheapflights users on 9/21. 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 1/26:59 pm -
1 stop4h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$440
This Delta deal was found by Cheapflights users on 9/21. 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.
Sun 1/36:00 am -
1 stop4h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$493
This Delta deal was found by Cheapflights users on 9/21. 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.
Mon 9/286:57 pm -
1 stop4h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$503
This Delta deal was found by Cheapflights users on 9/21. 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.
Mon 9/284:00 pm -
1 stop5h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$503
This American Airlines deal was found by Cheapflights users on 9/21. 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 1/25:11 pm -
1 stop6h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![American Airlines logo]()
$506
This Delta deal was found by Cheapflights users on 9/18. 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 10/86:03 am -
1 stop5h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Delta logo]()
$530
Find 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 September 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $429 (Delta) |
One-way from | $343 (Delta) |
Popular in | November |
Cheapest in | May |
Average price | $472 |
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 7,457,451 searches. Data last updated September 22, 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
Cheapest round-trip
GainesvilleChicago
GNV Gainesville Regional - MDW Chicago Midway
GNVMDW
Gainesville Regional
Wed 1/6
4:59 pm-10:10 pm
1 stop6h 11m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$343
GainesvilleChicago
GNV Gainesville Regional - ORD Chicago O'Hare Intl
GNVORD
Gainesville Regional
Mon 11/16
10:33 am-5:38 pm
1 stop8h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$343
Quickest round-trip
GainesvilleChicago
GNV Gainesville Regional - MDW Chicago Midway
GNVMDW
Gainesville Regional
Thu 12/31
6:00 am-9:13 am
1 stop4h 13m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$343
GainesvilleChicago
GNV Gainesville Regional - ORD Chicago O'Hare Intl
GNVORD
Gainesville Regional
Sun 11/8
6:00 am-11:05 am
1 stop6h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$343
GainesvilleChicago
GNV Gainesville Regional - MDW Chicago Midway
GNVMDW
Gainesville Regional
Thu 1/7
6:00 am-9:52 am
1 stop4h 52m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$343
GainesvilleChicago
GNV Gainesville Regional - MDW Chicago Midway
GNVMDW
Gainesville Regional
Fri 1/1
6:00 am-9:13 am
1 stop4h 13m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$343
GainesvilleChicago
GNV Gainesville Regional - MDW Chicago Midway
GNVMDW
Gainesville Regional
Wed 12/30
6:00 am-9:13 am
1 stop4h 13m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$343
GainesvilleChicago
GNV Gainesville Regional - ORD Chicago O'Hare Intl
GNVORD
Gainesville Regional
Tue 1/5
6:00 am-10:07 am
1 stop5h 07m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$343
GainesvilleChicago
GNV Gainesville Regional - ORD Chicago O'Hare Intl
GNVORD
Gainesville Regional
Wed 1/6
10:20 am-4:37 pm
1 stop7h 17m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$343
GainesvilleChicago
GNV Gainesville Regional - ORD Chicago O'Hare Intl
GNVORD
Gainesville Regional
Sun 10/25
7:03 pm-11:57 pm
1 stop5h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$343
Showing 1-10 of 34 resultsSorted by cheapest first
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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Gainesville-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Gainesville-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.
GNV-CHI
GNV-MDW
GNV-ORD
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
GNV-CHI
GNV-MDW
GNV-ORD
What is the cheapest month to book a flight from Gainesville to Chicago?
Currently, February is the cheapest month in which you can book a flight from Gainesville to Chicago (average of $407). Flying from Gainesville to Chicago in August is currently the most expensive (average of $814). 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.
How much does it cost to fly round-trip from Gainesville to Chicago?
Airfare is below average for this route at the moment.
Gainesville to Chicago flights typically cost between $450 and $484 in November.The cheapest round-trip price found within the last 5 days was $429 on Delta (Nov 3-Nov 7).
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 September 22, 2026.
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.
Entertainment
7.8
Food
7.2
Crew
8.5
Overall
7.8
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Entertainment
7.8
Food
7.2
Crew
8.5
Overall
7.8
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Entertainment
7.8
Food
7.2
Crew
8.5
Overall
7.8
Comfort
7.8
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 22, 2026.
Complete your trip
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Gainesville and Chicago flights
Browse other Gainesville and Chicago flight options. Last updated on September 22, 2026.
Other flights from Gainesville
Browse through other flights departing from Gainesville. Flights are based on user searches made on Cheapflights and were last updated on September 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated September 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$328 | Average$397 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$409 | Average$483 | FlexibilityNo cancel fee | On-time71% |