Cheap Flights from Gainesville to Chicago
Cheap Flights from Gainesville to Chicago
Looking for cheap flights from Gainesville to Chicago? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Gainesville to Chicago vary by season, cabin, and date, but available award flights can start around 7,500–9,000 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Gainesville to Chicago for specific travel dates.
2026-11-05
GNV - ORD
Economy | 1 Stop | 4 left
From 7,500 Pts + $25.6
2026-11-05
GNV - ORD
Economy | 1 Stop | 9+ left
From 7,500 Pts + $25.6
2026-11-05
GNV - ORD
Economy | 1 Stop | 4 left
From 7,500 Pts + $25.6
2026-11-12
GNV - ORD
Economy | 1 Stop | 9+ left
From 7,500 Pts + $25.6
2026-12-02
GNV - ORD
Economy | 1 Stop | 9+ left
From 7,500 Pts + $25.6
2026-11-27
GNV - ORD
Economy | 2 Stops
From 9,000 Pts + $5.6
Gainesville to Chicago flight facts
Distance
901 mi
1,450 km in a straight line
Estimated flight time
about 2h 15m
In the air, for the straight-line distance
Time difference
−1h
Chicago is 1 hour behind Gainesville.
Airports in Gainesville
GNV · Gainesville Regional
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Nearby airport alternatives
Flights Jacksonville - Chicago · Jacksonville is 66 mi from Gainesville
Flights Orlando - Chicago · Orlando is 105 mi from Gainesville
Flights Tampa - Chicago · Tampa is 120 mi from Gainesville
Flights Sarasota - Chicago · Sarasota is 159 mi from Gainesville
Flights Savannah - Chicago · Savannah is 180 mi from Gainesville
Premium cabin flights from Gainesville to Chicago
Premium cabin
2026-11-05
GNV - ORD
First | 1 Stop
From 21,500 Pts + $5.6
Premium cabin
2026-11-12
GNV - ORD
First | 1 Stop
From 23,500 Pts + $5.6
Premium cabin
2026-11-27
GNV - ORD
First | 2 Stops | 3 left
From 45,000 Pts + $25.6
Premium cabin
2026-11-27
GNV - ORD
First | 1 Stop | 8 left
From 47,100 Pts + $5.6
Premium cabin
2026-12-02
GNV - ORD
First | 1 Stop | 8 left
From 47,100 Pts + $5.6
Premium cabin
2026-11-05
GNV - ORD
Business | 1 Stop
From 29,000 Pts + $5.6
Selected hotels for your next stay
Chicago (United States)
Chicago Athletic Association
From 15,000 Pts or $236
Chicago (USA)
ACME Hotel Chicago, Outset Collection by Hilton
From 28,000 Pts or $75
Chicago, IL (USA)
Waldorf Astoria Chicago
From 95,000 Pts or $407
Frequently Asked Questions
The cheapest route from Gainesville to Chicago depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Gainesville to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Gainesville to Chicago.
Gainesville and Chicago are about 901 miles (1,450 km) apart in a straight line.
Flying the 901-mile straight-line distance takes about 2h 15m in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Chicago is 1 hour behind Gainesville.
Departures from Gainesville: Gainesville Regional (GNV). Arrivals in Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD).
Travelers searching this route also look at other popular routes into Chicago, plus the return trip when we track it. Fares and award space change daily.
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