Cheap Flights from Rochester to Chicago
Cheap Flights from Rochester to Chicago
Looking for cheap flights from Rochester 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 Rochester to Chicago vary by season, cabin, and date, but available award flights can start around 4,500 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 Rochester to Chicago for specific travel dates.
2026-11-07
RST - ORD
Economy | Non stop | 1 left
From 4,500 Pts + $25.6
2026-11-08
RST - ORD
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-11-09
RST - ORD
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-11-11
RST - ORD
Economy | Non stop | 5 left
From 4,500 Pts + $25.6
2026-11-14
RST - ORD
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
2026-11-15
RST - ORD
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
Rochester to Chicago flight facts
Distance
268 mi
432 km in a straight line
Estimated flight time
about 1h
In the air, for the straight-line distance
Time difference
Same time zone
Chicago is in the same time zone as Rochester.
Airports in Rochester
RST · Rochester Intl
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Nearby airport alternatives
Flights La Crosse - Chicago · La Crosse is 62 mi from Rochester
Flights Minneapolis - Chicago · Minneapolis is 76 mi from Rochester
Flights Eau Claire - Chicago · Eau Claire is 83 mi from Rochester
Flights Cedar Rapids - Chicago · Cedar Rapids is 145 mi from Rochester
Flights Wassau - Chicago · Wassau is 152 mi from Rochester
Flights Madison - Chicago · Madison is 167 mi from Rochester
Premium cabin flights from Rochester to Chicago
Premium cabin
2026-11-10
RST - ORD
First | Non stop | 5 left
From 9,000 Pts + $25.6
Premium cabin
2026-11-12
RST - ORD
First | Non stop | 5 left
From 9,000 Pts + $25.6
Premium cabin
2026-11-16
RST - ORD
First | Non stop | 8 left
From 9,000 Pts + $25.6
Premium cabin
2026-11-17
RST - ORD
First | Non stop | 4 left
From 9,000 Pts + $25.6
Premium cabin
2026-11-19
RST - ORD
First | Non stop | 1 left
From 9,000 Pts + $25.6
Premium cabin
2026-11-22
RST - ORD
First | Non stop | 6 left
From 9,000 Pts + $25.6
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 Rochester 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 Rochester to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Rochester to Chicago.
Rochester and Chicago are about 268 miles (432 km) apart in a straight line.
Flying the 268-mile straight-line distance takes about 1h in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Chicago is in the same time zone as Rochester.
Departures from Rochester: Rochester Intl (RST). 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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points travel planning experience. Yeah!
