$208+ Cheap flights from Ottawa (YOW) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — CHI
Sep 1 — Sep 81
Round-trip
1 adult, Economy
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Find cheap flights from Ottawa to Chicago with Cheapflights
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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Ottawa to Chicago
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Cheapest flights from Ottawa to ChicagoExplore the most affordable flight options available from Ottawa to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 2, 2026.
Explore the most affordable flight options available from Ottawa to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:00 am
YOW
- MDW
1 stop8h 35m
Porter Airlines
Sat 9/1211:45 am
MDW
- YOW
1 stop6h 22m
Porter Airlines
Deal found 7/29![Porter Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:25 pm
YOW
- MDW
1 stop17h 35m
Multiple Airlines
Mon 9/213:20 pm
MDW
- YOW
1 stop15h 45m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/67:20 am
YOW
- ORD
1 stop10h 20m
WestJet
Sun 9/135:30 pm
ORD
- YOW
1 stop11h 05m
WestJet
Deal found 7/30![WestJet logo]()
$378
This American Airlines deal was found by Cheapflights users on 8/1. 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.
Tue 9/157:00 am
YOW
- ORD
1 stop6h 45m
American Airlines
Tue 9/228:03 am
ORD
- YOW
1 stop5h 52m
American Airlines
Deal found 8/1![American Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:00 am
YOW
- ORD
1 stop16h 59m
Multiple Airlines
Sat 9/1912:56 pm
ORD
- YOW
2 stops49h 19m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$389
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:55 am
YOW
- ORD
1 stop9h 00m
Multiple Airlines
Fri 9/189:55 am
ORD
- YOW
1 stop6h 40m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:55 am
YOW
- MDW
1 stop8h 40m
Multiple Airlines
Sun 9/2011:45 am
MDW
- YOW
1 stop11h 35m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$400
This Trip.com deal was found by Cheapflights users on 7/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:55 am
YOW
- ORD
1 stop13h 53m
Multiple Airlines
Sat 9/123:45 pm
ORD
- YOW
1 stop7h 35m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$402
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:00 am
YOW
- ORD
2 stops16h 59m
Multiple Airlines
Sun 9/207:11 am
ORD
- YOW
1 stop31h 04m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/69:05 am
YOW
- ORD
2 stops23h 48m
Multiple Airlines
Sun 9/137:11 am
ORD
- YOW
1 stop31h 04m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$404
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:45 pm
YOW
- MDW
1 stop14h 00m
Porter Airlines
Fri 10/163:20 pm
MDW
- YOW
1 stop20h 32m
Porter Airlines
Deal found 7/30![Porter Airlines logo]()
$407
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:10 pm
YOW
- MDW
2 stops21h 45m
Multiple Airlines
Wed 9/211:45 am
MDW
- YOW
1 stop5h 07m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$409
Best flights from Ottawa to ChicagoDiscover carefully curated flight deals from Ottawa to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 2, 2026.
Discover carefully curated flight deals from Ottawa to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:25 pm
YOW
- MDW
1 stop17h 35m
Multiple Airlines
Sun 9/2011:45 am
MDW
- YOW
1 stop11h 35m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1010:40 am
YOW
- MDW
1 stop4h 55m
Porter Airlines
Sat 9/1211:45 am
MDW
- YOW
1 stop6h 22m
Porter Airlines
Deal found 7/28![Porter Airlines logo]()
$447
This United Airlines deal was found by Cheapflights users on 7/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:05 am
YOW
- ORD
1 stop15h 02m
United Airlines
Wed 9/25:00 am
ORD
- YOW
1 stop16h 35m
United Airlines
Deal found 7/30![United Airlines logo]()
$597
This FlightHub deal was found by Cheapflights users on 7/31. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:50 am
YOW
- ORD
2 stops13h 30m
WestJet
Fri 10/235:30 pm
ORD
- YOW
1 stop11h 05m
WestJet
Deal found 7/31![WestJet logo]()
$620
This FlightHub deal was found by Cheapflights users on 7/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2710:40 am
YOW
- MDW
1 stop4h 55m
Porter Airlines
Fri 9/43:20 pm
MDW
- YOW
1 stop5h 22m
Porter Airlines
Deal found 7/30![Porter Airlines logo]()
$541
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/272:10 pm
YOW
- ORD
2 stops18h 43m
Multiple Airlines
Fri 9/49:10 pm
ORD
- YOW
1 stop16h 23m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$544
This Porter Airlines deal was found by Cheapflights users on 8/1. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/114:00 pm
YOW
- ORD
1 stop5h 20m
Porter Airlines
Tue 9/158:03 am
ORD
- YOW
1 stop5h 52m
Porter Airlines
Deal found 8/1![Porter Airlines logo]()
$563
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:00 am
YOW
- MDW
2 stops15h 58m
Multiple Airlines
Sat 10/1011:45 am
MDW
- YOW
1 stop6h 22m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$572
This United Airlines deal was found by Cheapflights users on 7/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:25 am
YOW
- ORD
Nonstop2h 19m
United Airlines
Sun 8/3010:40 am
ORD
- YOW
Nonstop2h 19m
United Airlines
Deal found 7/28![United Airlines logo]()
$680
This Porter Airlines deal was found by Cheapflights users on 7/28. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:40 am
YOW
- ORD
1 stop6h 40m
Porter Airlines
Wed 10/288:45 pm
ORD
- YOW
1 stop20h 13m
Porter Airlines
Deal found 7/28![Porter Airlines logo]()
$565
This FlightHub deal was found by Cheapflights users on 7/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:55 am
YOW
- MDW
2 stops6h 44m
WestJet
Mon 10/510:48 am
MDW
- YOW
2 stops12h 32m
WestJet
Deal found 7/29![WestJet logo]()
$690
This United Airlines deal was found by Cheapflights users on 7/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:25 am
YOW
- ORD
Nonstop2h 19m
United Airlines
Wed 10/2810:57 am
ORD
- YOW
Nonstop2h 12m
United Airlines
Deal found 7/28![United Airlines logo]()
$685
This FlightHub deal was found by Cheapflights users on 7/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:55 am
YOW
- MDW
2 stops6h 44m
WestJet
Mon 10/510:48 am
MDW
- YOW
2 stops12h 32m
WestJet
Deal found 7/29![WestJet logo]()
$691
This Porter Airlines deal was found by Cheapflights users on 7/29. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2810:40 am
YOW
- MDW
1 stop4h 55m
Porter Airlines
Tue 9/2911:45 am
MDW
- YOW
1 stop5h 07m
Porter Airlines
Deal found 7/29![Porter Airlines logo]()
$604
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/157:00 am
YOW
- MDW
2 stops16h 03m
Multiple Airlines
Fri 8/213:15 pm
MDW
- YOW
1 stop3h 49m
Multiple Airlines
Deal found 8/2![Multiple Airlines logo]()
$670
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:20 pm
YOW
- ORD
Nonstop2h 26m
United Airlines
Mon 10/510:40 am
ORD
- YOW
Nonstop2h 19m
United Airlines
Deal found 7/29![United Airlines logo]()
$685
This Mytrip deal was found by Cheapflights users on 7/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:45 pm
YOW
- MDW
1 stop13h 55m
Porter Airlines
Fri 9/43:20 pm
MDW
- YOW
1 stop3h 42m
Porter Airlines
Deal found 7/31![Porter Airlines logo]()
$605
This United Airlines deal was found by Cheapflights users on 7/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:20 pm
YOW
- ORD
Nonstop2h 26m
United Airlines
Tue 9/810:40 am
ORD
- YOW
Nonstop2h 19m
United Airlines
Deal found 7/28![United Airlines logo]()
$686
This United deal was found by Cheapflights users on 7/29. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:00 am
YOW
- ORD
2 stops7h 56m
Multiple Airlines
Sun 8/302:00 pm
ORD
- YOW
1 stop4h 52m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$686
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:25 am
YOW
- ORD
Nonstop2h 19m
United Airlines
Sun 8/306:15 pm
ORD
- YOW
1 stop4h 39m
United Airlines
Deal found 7/29![United Airlines logo]()
$686
This United Airlines deal was found by Cheapflights users on 7/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:20 pm
YOW
- ORD
Nonstop2h 26m
United Airlines
Fri 10/236:21 pm
ORD
- YOW
Nonstop2h 14m
United Airlines
Deal found 7/31![United Airlines logo]()
$689
Last-minute flights from Ottawa to ChicagoDiscover last-minute flight deals from Ottawa to Chicago. Data last updated August 2, 2026 and is based on user searches.
Discover last-minute flight deals from Ottawa to Chicago. Data last updated August 2, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:45 pm
YOW
- MDW
1 stop14h 00m
Porter Airlines
Fri 10/163:20 pm
MDW
- YOW
1 stop20h 32m
Porter Airlines
Deal found 7/30![Porter Airlines logo]()
$407
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:45 pm
YOW
- MDW
1 stop14h 00m
Porter Airlines
Sat 10/311:45 am
MDW
- YOW
1 stop6h 22m
Porter Airlines
Deal found 7/30![Porter Airlines logo]()
$420
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:45 pm
YOW
- MDW
1 stop14h 00m
Porter Airlines
Thu 10/83:20 pm
MDW
- YOW
1 stop19h 07m
Porter Airlines
Deal found 7/30![Porter Airlines logo]()
$449
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:45 pm
YOW
- MDW
1 stop14h 00m
Porter Airlines
Tue 10/611:45 am
MDW
- YOW
1 stop5h 07m
Porter Airlines
Deal found 7/30![Porter Airlines logo]()
$452
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:45 pm
YOW
- MDW
1 stop14h 00m
Porter Airlines
Sun 10/1811:45 am
MDW
- YOW
1 stop5h 07m
Porter Airlines
Deal found 7/30![Porter Airlines logo]()
$453
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:45 pm
YOW
- MDW
1 stop14h 00m
Porter Airlines
Wed 10/711:45 am
MDW
- YOW
1 stop5h 07m
Porter Airlines
Deal found 7/30![Porter Airlines logo]()
$454
This American Airlines deal was found by Cheapflights users on 7/28. 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 8/208:40 am
YOW
- ORD
1 stop6h 40m
American Airlines
Sun 8/238:09 am
ORD
- YOW
1 stop5h 46m
American Airlines
Deal found 7/28![American Airlines logo]()
$441
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/252:10 pm
YOW
- ORD
2 stops18h 43m
Multiple Airlines
Sun 8/308:05 am
ORD
- YOW
1 stop29h 50m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$436
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:10 pm
YOW
- MDW
2 stops21h 45m
Multiple Airlines
Wed 9/211:45 am
MDW
- YOW
1 stop5h 07m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$409
This FlightHub deal was found by Cheapflights users on 7/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/268:00 am
YOW
- MDW
1 stop7h 35m
Porter Airlines
Wed 9/211:45 am
MDW
- YOW
1 stop5h 07m
Porter Airlines
Deal found 7/29![Porter Airlines logo]()
$429
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:45 pm
YOW
- MDW
1 stop13h 55m
Porter Airlines
Mon 8/3110:25 am
MDW
- YOW
1 stop25h 27m
Porter Airlines
Deal found 8/1![Porter Airlines logo]()
$428
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2810:40 am
YOW
- MDW
1 stop4h 55m
Porter Airlines
Sun 8/3010:20 am
MDW
- YOW
1 stop6h 34m
Porter Airlines
Deal found 8/2![Porter Airlines logo]()
$450
One-way flights from Ottawa to ChicagoSearch for one-way flight options from Ottawa to Chicago. Find affordable one-way fares based on user searches. Data last updated August 2, 2026.
Search for one-way flight options from Ottawa to Chicago. Find affordable one-way fares based on user searches. Data last updated August 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:00 am
YOW
- MDW
1 stop8h 35m
Porter Airlines
Deal found 7/31![Porter Airlines logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/247:00 am
YOW
- ORD
1 stop30h 50m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/282:10 pm
YOW
- ORD
2 stops29h 13m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$216
This American Airlines deal was found by Cheapflights users on 8/2. 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 9/97:00 am
YOW
- ORD
1 stop6h 44m
American Airlines
Deal found 8/2![American Airlines logo]()
$225
This American Airlines deal was found by Cheapflights users on 7/28. 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 9/118:40 am
YOW
- ORD
1 stop6h 40m
American Airlines
Deal found 7/28![American Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:05 am
YOW
- ORD
2 stops23h 48m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:55 pm
YOW
- MDW
1 stop18h 05m
Porter Airlines
Deal found 7/31![Porter Airlines logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/283:30 pm
YOW
- MDW
1 stop20h 30m
Porter Airlines
Deal found 7/31![Porter Airlines logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2812:25 pm
YOW
- MDW
3 stops47h 35m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/281:20 pm
YOW
- MDW
3 stops34h 27m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/192:30 pm
YOW
- MDW
2 stops33h 17m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$272
This Trip.com deal was found by Cheapflights users on 7/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2710:40 am
YOW
- MDW
1 stop4h 55m
Porter Airlines
Deal found 7/30![Porter Airlines logo]()
$276
Find flight deals from Ottawa to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Ottawa (YOW) 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 August 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $361 (Kiwi.com) |
One-way from | $208 (Kiwi.com) |
Popular in | January |
Cheapest in | February |
Average price | $459 |
Good round-trip deal | $484 or less |
Good one-way deal | $314 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Ottawa 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 2,558,603 searches. Data last updated August 2, 2026.
Use the filters below to find and compare flights from Ottawa to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OttawaChicago
YOW - MDW
YOWMDW
Ottawa
Tue 9/15
6:25 pm-11:00 am
1 stop17h 35m
Chicago Midway
Sun 9/20
11:45 am-12:20 am
1 stop11h 35m
$413
OttawaChicago
YOW - MDW
YOWMDW
Ottawa
Thu 9/10
10:40 am-2:35 pm
1 stop4h 55m
Chicago Midway
Sat 9/12
11:45 am-7:07 pm
1 stop6h 22m
$447
OttawaChicago
YOW - MDW
YOWMDW
Ottawa
Thu 8/27
10:40 am-2:35 pm
1 stop4h 55m
Chicago Midway
Fri 9/4
3:20 pm-9:42 pm
1 stop5h 22m
$541
OttawaChicago
YOW - ORD
YOWORD
Ottawa
Thu 8/27
2:10 pm-7:53 am
2 stops18h 43m
Chicago O'Hare Intl
Fri 9/4
9:10 pm-2:33 pm
1 stop16h 23m
$544
OttawaChicago
YOW - ORD
YOWORD
Ottawa
Fri 9/11
4:00 pm-8:20 pm
1 stop5h 20m
Chicago O'Hare Intl
Tue 9/15
8:03 am-2:55 pm
1 stop5h 52m
$563
OttawaChicago
YOW - ORD
YOWORD
Ottawa
Sat 10/24
8:40 am-2:20 pm
1 stop6h 40m
Chicago O'Hare Intl
Wed 10/28
8:45 pm-5:58 pm
1 stop20h 13m
$565
OttawaChicago
YOW - MDW
YOWMDW
Ottawa
Fri 10/9
7:00 am-9:58 pm
2 stops15h 58m
Chicago Midway
Sat 10/10
11:45 am-7:07 pm
1 stop6h 22m
$572
OttawaChicago
YOW - ORD
YOWORD
Ottawa
Wed 8/26
6:05 am-8:07 pm
1 stop15h 02m
Chicago O'Hare Intl
Wed 9/2
5:00 am-10:35 pm
1 stop16h 35m
$597
OttawaChicago
YOW - MDW
YOWMDW
Ottawa
Mon 9/28
10:40 am-2:35 pm
1 stop4h 55m
Chicago Midway
Tue 9/29
11:45 am-5:52 pm
1 stop5h 07m
$604
OttawaChicago
YOW - MDW
YOWMDW
Ottawa
Fri 8/28
8:45 pm-9:40 am
1 stop13h 55m
Chicago Midway
Fri 9/4
3:20 pm-8:02 pm
1 stop3h 42m
$605
Showing 1-10 of 42 resultsSorted by cheapest first
Compare providers for flights from Ottawa 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 Ottawa to Chicago in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Ottawa-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Ottawa-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Ottawa-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Ottawa-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 Ottawa-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 Ottawa to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Ottawa with our price prediction graph.
YOW-CHI
YOW-MDW
YOW-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 Ottawa to Chicago
YOW-CHI
YOW-MDW
YOW-ORD
What is the cheapest month to book a flight from Ottawa to Chicago?
Currently, September is the cheapest month in which you can book a flight from Ottawa to Chicago (average of $377). Flying from Ottawa to Chicago in January is currently the most expensive (average of $806). 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.
What is the cheapest time of day to fly from YOW to CHI?
Find hourly flight availability from Ottawa to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 2, 2026.
When flying from Ottawa to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Ottawa to Chicago
Explore weekly flight availability from Ottawa to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 2, 2026.
The most flights from YOW to CHI are scheduled on a Monday (12 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).
How much does it cost to fly round-trip from Ottawa to Chicago?
Airfare is typical for this route at the moment.
Ottawa to Chicago flights typically cost between $354 and $470 in September.The cheapest round-trip price found within the last 5 days was $361 on Porter Airlines (Sep 5-Sep 12).
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 August 2, 2026.
Peruse reviews from past customers who have flown with Porter Airlines and United Airlines from Ottawa to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Entertainment
6.9
Overall
8.0
Boarding
8.2
Crew
8.6
Food
7.5
Reviews
1 / 20
6.0
GoodShannon,Jul 2026
YQT - YOW
Comfort
8.0
Entertainment
6.9
Overall
8.0
Boarding
8.2
Crew
8.6
Food
7.5
Reviews
1 / 20
6.0
GoodShannon,Jul 2026
YQT - YOW
Comfort
8.0
Entertainment
6.9
Overall
8.0
Boarding
8.2
Crew
8.6
Food
7.5
Reviews
1 / 20
6.0
GoodShannon,Jul 2026
YQT - YOW
Related info for your journey
Find useful and relevant information for your journey from Ottawa 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 August 2, 2026.
Complete your trip
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Ottawa and Chicago flights
Browse other Ottawa and Chicago flight options. Last updated on August 2, 2026.
Other flights from Ottawa
Browse through other flights departing from Ottawa. Flights are based on user searches made on Cheapflights and were last updated on August 2, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Ottawa to Chicago
Discover the top airline that operate flights from Ottawa 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 2,558,603 searches. Data last updated August 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$520 | Average$689 | FlexibilityNo cancel fee | On-time69% |