Cheap Flights from Ottawa to Chicago
Cheap Flights from Ottawa to Chicago
Looking for cheap flights from Ottawa 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 Ottawa to Chicago vary by season, cabin, and date, but available award flights can start around 11,531–49,000 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 Ottawa to Chicago for specific travel dates.
2026-12-26
YOW - ORD
Economy | 1 Stop | 9+ left
From 11,531 Pts + $180.4
2026-12-27
YOW - ORD
Economy | 1 Stop | 9+ left
From 17,656 Pts + $180.4
2026-12-26
YOW - ORD
Business | 1 Stop | 5 left
From 23,061 Pts + $180.4
2026-12-26
YOW - ORD
Premium Economy | 1 Stop | 2 left
From 27,500 Pts + $101
2026-12-27
YOW - ORD
Premium Economy | 1 Stop | 6 left
From 27,500 Pts + $101.3
2026-12-26
YOW - ORD
Business | Non stop | 9+ left
From 49,000 Pts + $62.9
Ottawa to Chicago flight facts
Distance
659 mi
1,060 km in a straight line
Estimated flight time
about 1h 45m
In the air, for the straight-line distance
Time difference
−1h
Chicago is 1 hour behind Ottawa.
Airports in Ottawa
YOW · Ottawa Macdonald-Cartier Intl
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Nearby airport alternatives
Flights Montreal - Chicago · Montreal is 95 mi from Ottawa
Flights Ottawa - Madison · Madison is 111 mi from Chicago
Flights Burlington - Chicago · Burlington is 136 mi from Ottawa
Flights Syracuse - Chicago · Syracuse is 154 mi from Ottawa
Flights Rochester - Chicago · Rochester is 182 mi from Ottawa
Premium cabin flights from Ottawa to Chicago
Premium cabin
2026-12-27
YOW - ORD
Business | Non stop | 9+ left
From 49,300 Pts + $63.1
Premium cabin
2026-12-26
YOW - ORD
First | 1 Stop | 5 left
From 49,000 Pts + $68.5
Premium cabin
2026-12-26
YOW - ORD
Business | 1 Stop | 5 left
From 23,061 Pts + $180.4
Premium cabin
2026-12-26
YOW - ORD
Business | Non stop | 9+ left
From 49,000 Pts + $62.9
Premium cabin
2026-12-26
YOW - ORD
Premium Economy | 1 Stop | 2 left
From 27,500 Pts + $101
Premium cabin
2026-12-27
YOW - ORD
Premium Economy | 1 Stop | 6 left
From 27,500 Pts + $101.3
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 Ottawa 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 Ottawa to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Ottawa to Chicago.
Ottawa and Chicago are about 659 miles (1,060 km) apart in a straight line.
Flying the 659-mile straight-line distance takes about 1h 45m 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 Ottawa.
Departures from Ottawa: Ottawa Macdonald-Cartier Intl (YOW). 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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