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Everything you should know
Flight Deals
Cheap Flights from Ottawa to Chicago (YOW-CHI)
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Ottawa to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.
Recent round-trip flight deals from Ottawa to Chicago
Fri, 4 Dec - Sun, 6 Dec
12:15 p.m. - 5:40 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
6h 25m1 stop Toronto Island
12:15 p.m. - 6:13 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
4h 58m1 stop Toronto Island
C$ 527Porter Airlines
Sat, 5 Dec - Sun, 6 Dec
12:40 p.m. - 5:40 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
6h 00m1 stop Toronto Island
12:15 p.m. - 6:13 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
4h 58m1 stop Toronto Island
C$ 534Porter Airlines
Fri, 11 Dec - Mon, 14 Dec
12:15 p.m. - 5:40 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
6h 25m1 stop Toronto Island
12:15 p.m. - 6:13 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
4h 58m1 stop Toronto Island
C$ 535Porter Airlines
Fri, 4 Dec - Sun, 6 Dec
12:15 p.m. - 5:40 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
6h 25m1 stop Toronto Island
12:15 p.m. - 6:13 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
4h 58m1 stop Toronto Island
C$ 535Porter Airlines
Sat, 5 Dec - Sun, 6 Dec
12:40 p.m. - 5:40 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
6h 00m1 stop Toronto Island
12:15 p.m. - 6:13 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
4h 58m1 stop Toronto Island
C$ 535Porter Airlines
Thu, 3 Dec - Thu, 10 Dec
12:15 p.m. - 5:40 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
6h 25m1 stop Toronto Island
12:15 p.m. - 6:13 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
4h 58m1 stop Toronto Island
C$ 537Porter Airlines
Thu, 26 Nov - Fri, 27 Nov
12:15 p.m. - 5:40 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
6h 25m1 stop Toronto Island
12:15 p.m. - 6:12 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
4h 57m1 stop Toronto Island
C$ 537Porter Airlines
Sat, 5 Dec - Mon, 7 Dec
12:40 p.m. - 5:40 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
6h 00m1 stop Toronto Island
12:15 p.m. - 6:13 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
4h 58m1 stop Toronto Island
C$ 537Porter Airlines
Sun, 20 Dec - Sun, 27 Dec
9:00 a.m. - 3:02 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
7h 02m1 stop Montreal Pierre Elliott Trudeau Intl
4:30 p.m. - 9:50 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
4h 20m1 stop Toronto Pearson Intl
C$ 959Air Canada
Fri, 18 Dec - Fri, 1 Jan
2:55 p.m. - 7:52 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
5h 57m1 stop Montreal Pierre Elliott Trudeau Intl
12:50 p.m. - 6:45 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
4h 55m1 stop Toronto Pearson Intl
C$ 971Air Canada
Recent one-way flight deals from Ottawa to Chicago
Sun, 10 Jan
3:25 p.m. - 3:03 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
24h 38m1 stop Fort Lauderdale
C$ 289Multiple Airlines
Sun, 10 Jan
3:25 p.m. - 3:03 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
24h 38m1 stop Fort Lauderdale
C$ 291Multiple Airlines
Sun, 10 Jan
3:25 p.m. - 3:03 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
24h 38m1 stop Fort Lauderdale
C$ 293Multiple Airlines
Sun, 10 Jan
5:30 a.m. - 3:03 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
34h 33m2 stops Toronto Pearson Intl Fort Lauderdale
C$ 298Multiple Airlines
Sun, 10 Jan
3:25 p.m. - 3:03 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
24h 38m1 stop Fort Lauderdale
C$ 300Multiple Airlines
Sun, 10 Jan
3:25 p.m. - 3:03 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
24h 38m1 stop Fort Lauderdale
C$ 305Multiple Airlines
Mon, 11 Jan
5:30 a.m. - 4:14 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
35h 44m2 stops Toronto Pearson Intl Fort Lauderdale
C$ 310Multiple Airlines
Mon, 11 Jan
5:30 a.m. - 4:14 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
35h 44m2 stops Toronto Pearson Intl Fort Lauderdale
C$ 313Multiple Airlines
Wed, 16 Dec
4:36 p.m. - 6:20 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
2h 44mdirect
C$ 567Air Canada
Sat, 9 Jan
6:15 a.m. - 8:00 a.m.YOW Ottawa-ORD Chicago O'Hare Intl
2h 45mdirect
C$ 574Air Canada
Recent last minute flight deals from Ottawa to Chicago
Tue, 10 Nov - Mon, 7 Dec
8:00 a.m. - 5:07 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
10h 07m1 stop Orlando
12:15 p.m. - 6:13 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
4h 58m1 stop Toronto Island
C$ 803Multiple Airlines
Tue, 10 Nov - Mon, 7 Dec
8:00 a.m. - 6:30 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
11h 30m2 stops Orlando Atlanta Hartsfield-Jackson
12:15 p.m. - 6:13 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
4h 58m1 stop Toronto Island
C$ 817Multiple Airlines
Tue, 10 Nov - Mon, 16 Nov
8:00 a.m. - 5:07 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
10h 07m1 stop Orlando
1:04 p.m. - 5:24 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
27h 20m2 stops Houston George Bush Intcntl Fort Lauderdale
C$ 830Multiple Airlines
Tue, 10 Nov - Mon, 7 Dec
8:00 a.m. - 5:47 p.m.YOW Ottawa-MDW Chicago Midway
10h 47m2 stops Orlando Atlanta Hartsfield-Jackson
5:02 p.m. - 11:33 a.m.MDW Chicago Midway-YOW Ottawa
17h 31m3 stops Atlanta Hartsfield-Jackson Newark Toronto Island
C$ 866Multiple Airlines
Tue, 10 Nov - Mon, 16 Nov
8:00 a.m. - 5:07 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
10h 07m1 stop Orlando
7:55 a.m. - 5:24 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
8h 29m1 stop Fort Lauderdale
C$ 880Multiple Airlines
Tue, 10 Nov - Mon, 7 Dec
8:00 a.m. - 6:30 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
11h 30m2 stops Orlando Atlanta Hartsfield-Jackson
10:29 p.m. - 2:32 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
15h 03m2 stops Atlanta Hartsfield-Jackson Newark
C$ 905Multiple Airlines
Wed, 11 Nov - Mon, 16 Nov
8:00 a.m. - 5:07 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
10h 07m1 stop Orlando
7:55 a.m. - 5:24 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
8h 29m1 stop Fort Lauderdale
C$ 908Multiple Airlines
Wed, 11 Nov - Mon, 16 Nov
8:00 a.m. - 12:21 a.m.YOW Ottawa-ORD Chicago O'Hare Intl
17h 21m2 stops Orlando Denver Intl
7:55 a.m. - 5:24 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
8h 29m1 stop Fort Lauderdale
C$ 921Multiple Airlines
Tue, 10 Nov - Mon, 16 Nov
8:00 a.m. - 5:07 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
10h 07m1 stop Orlando
5:15 p.m. - 5:52 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
23h 37m3 stops Las Vegas Harry Reid Intl Orlando Toronto Pearson Intl
C$ 947Multiple Airlines
Tue, 10 Nov - Mon, 7 Dec
6:15 a.m. - 8:00 a.m.YOW Ottawa-ORD Chicago O'Hare Intl
2h 45mdirect
1:55 p.m. - 7:52 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
4h 57m1 stop Toronto Island
C$ 1,182Air Canada
Recent direct flight deals from Ottawa to Chicago
Fri, 4 Dec - Sun, 6 Dec
6:15 a.m. - 8:00 a.m.YOW Ottawa-ORD Chicago O'Hare Intl
2h 45mdirect
10:57 a.m. - 2:09 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
2h 12mdirect
C$ 950Lufthansa
Sat, 5 Dec - Sun, 6 Dec
6:15 a.m. - 8:00 a.m.YOW Ottawa-ORD Chicago O'Hare Intl
2h 45mdirect
10:57 a.m. - 2:09 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
2h 12mdirect
C$ 952Lufthansa
Tue, 8 Dec - Wed, 9 Dec
6:15 a.m. - 8:00 a.m.YOW Ottawa-ORD Chicago O'Hare Intl
2h 45mdirect
10:57 a.m. - 2:09 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
2h 12mdirect
C$ 954United Airlines
Tue, 15 Dec - Wed, 30 Dec
6:15 a.m. - 8:00 a.m.YOW Ottawa-ORD Chicago O'Hare Intl
2h 45mdirect
10:48 a.m. - 2:09 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
2h 21mdirect
C$ 956United Airlines
Thu, 17 Dec - Wed, 30 Dec
4:42 p.m. - 6:30 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
2h 48mdirect
10:48 a.m. - 2:09 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
2h 21mdirect
C$ 956United Airlines
Tue, 15 Dec - Thu, 31 Dec
4:36 p.m. - 6:20 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
2h 44mdirect
5:56 p.m. - 9:23 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
2h 27mdirect
C$ 956United Airlines
Sat, 19 Dec - Thu, 31 Dec
6:15 a.m. - 8:00 a.m.YOW Ottawa-ORD Chicago O'Hare Intl
2h 45mdirect
5:56 p.m. - 9:23 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
2h 27mdirect
C$ 956United Airlines
Sun, 20 Dec - Thu, 31 Dec
6:15 a.m. - 8:00 a.m.YOW Ottawa-ORD Chicago O'Hare Intl
2h 45mdirect
5:56 p.m. - 9:23 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
2h 27mdirect
C$ 956United Airlines
Thu, 3 Dec - Sun, 6 Dec
4:36 p.m. - 6:20 p.m.YOW Ottawa-ORD Chicago O'Hare Intl
2h 44mdirect
5:58 p.m. - 9:16 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
2h 18mdirect
C$ 1,061Air Canada
Sat, 5 Dec - Sun, 6 Dec
6:15 a.m. - 8:00 a.m.YOW Ottawa-ORD Chicago O'Hare Intl
2h 45mdirect
5:58 p.m. - 9:16 p.m.ORD Chicago O'Hare Intl-YOW Ottawa
2h 18mdirect
C$ 1,070Air Canada
Booking Insights
Price, demand, and travel trends for Ottawa to Chicago flights
Use KAYAK data on prices, travel dates, airlines, and seasonal trends to compare options and book flights with more confidence.
Prices
Airlines
Layovers
More
How much is a round-trip flight from Ottawa to Chicago?
This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Ottawa to Chicago departing in december.What is the cheapest Ottawa to Chicago flight route?
KAYAK tracks online flight deals over the last 12 months and analyzes pricing trends to identify the best available fares.Ottawa (YOW) to Chicago Midway Airport (MDW) is the cheapest Ottawa to Chicago route, averaging C$ 599 round-trip. Other Ottawa to Chicago routes average C$ 986, based on KAYAK data over the past 12 months.
What's the cheapest day of the week to fly from Ottawa to Chicago?
Based on deals KAYAK users found in the last 12 months, Sunday is the cheapest day of the week to fly from Ottawa to Chicago. It's 21% cheaper than the average day, while Monday is the most expensive, with prices 16% higher.
Round-trip flights from Ottawa to Chicago typically range from C$ 637 to C$ 1,097. The lowest price found in the past 5 days was C$ 527, on Porter Airlines.
Which airline is the cheapest to fly from Ottawa to Chicago?
Porter Airlines (C$ 527) and Air Canada (C$ 959) are the cheapest airlines to fly round-trip from Ottawa to Chicago according to KAYAK data over the last 5 days.
Which airline offers the most direct flights between Ottawa and Chicago?
United Airlines has the most frequent direct flights from Ottawa to Chicago with 14 flights per week. Based on KAYAK flight data over the last 3 months.
What’s the most popular layover airport when flying from Ottawa to Chicago?
KAYAK data for 1-stop round-trips over the past 3 months. Only counts itineraries with the same layover on both legs.Toronto Island (YTZ) is the most popular layover for the Ottawa to Chicago route. 80% of KAYAK users who booked 1-stop round-trips over the past 3 months connected via YTZ.
What is the cheapest layover airport when flying from Ottawa to Chicago?
Flights via Fort Lauderdale (FLL) offer the most affordable fares, with an average round-trip price of C$ 492. Based on KAYAK data over the past 3 months.
Which route with a layover is the fastest from Ottawa to Chicago?
Toronto Island (YTZ) offers the shortest 1-stop connection from Ottawa to Chicago at 4h 57m one-way, 2h 11m longer than the 2h 46m direct flight. Based on KAYAK data over the past 3 months.
When flying from Ottawa to Chicago, which airport offers the shortest layover?
Toronto Island (YTZ) had the shortest average connection time for Ottawa to Chicago layovers at 3h 34m over the past three months.
How many direct flights run daily between Ottawa and Chicago?
There are about 2 flights per day from Ottawa to Chicago, which is about 14 flights per week, spread evenly across the week.
What time of day do most flights depart from Ottawa to Chicago?
Based on KAYAK flight schedules for the upcoming 3 months.Most direct flights from Ottawa to Chicago depart in the morning, accounting for 50% of direct departures. Around 1 flights are scheduled in that window over the next three months.
Expert advice
Expert advice for your flight from Ottawa to Chicago
AI-powered summary based on content written by travel experts. AI can make mistakes.
Our travel experts
Key details for Ottawa to Chicago flights
Low season | February |
|---|---|
High season | September |
Cheapest flight | C$ 289 |
When to book flights from Ottawa to Chicago
Are your dates flexible? Find out the best times to travel from Ottawa to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.
Your Ottawa to Chicago flight questions, answered
Find helpful answers about this route, including flight times, airports, airlines, and booking tips.
Your guide to booking Ottawa to Chicago flights
Get tips on when to book, when to fly, and what to know before your trip.Prefer to fly direct from Ottawa to Chicago?
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Ottawa to Chicago.
Direct departures
Ottawa to Chicago
Monday
United Airlines
United Airlines
Tuesday
United Airlines
United Airlines
Wednesday
United Airlines
United Airlines
Thursday
United Airlines
United Airlines
Friday
United Airlines
United Airlines
Saturday
United Airlines
United Airlines
Sunday
United Airlines
United Airlines
Direct returns
Chicago to Ottawa
Monday
United Airlines
United Airlines
Tuesday
United Airlines
United Airlines
Wednesday
United Airlines
United Airlines
Thursday
United Airlines
United Airlines
Friday
United Airlines
United Airlines
Saturday
United Airlines
United Airlines
Sunday
United Airlines
United Airlines
More options for your flight from Ottawa to Chicago
Complete your trip to Chicago with a hotel stay or car rental
Information on your arrival and departure airports
Cabin class types available on flights from Ottawa to Chicago
Cabin classes available on flights from Ottawa to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.
First Class flights from Ottawa to Chicagofrom C$ 3,838
Business Class flights from Ottawa to Chicagofrom C$ 2,457
Premium Economy Class flights from Ottawa to Chicagofrom C$ 2,417
Economy Class flights from Ottawa to Chicagofrom C$ 524
Find direct flights to and from Ottawa and Chicago
Flights from domestic origins to Chicago
More flights to Chicago. Prices are the lowest found on KAYAK in the last 7 days. Price and availability are not guaranteed.
Choose which airport to fly into in Chicago
Ottawa to Chicago Midway Airportfrom C$ 783
Ottawa to Chicago O'Hare Intl Airportfrom C$ 535
Flights to other popular destinations
The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.