$193+ 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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — CHI
Aug 21 — Aug 281
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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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 July 22, 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 July 22, 2026.
This Trip.com deal was found by Cheapflights users on 7/19. 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.
Fri 9/256:55 am
YOW
- ORD
1 stop7h 28m
Multiple Airlines
Tue 9/292:15 pm
ORD
- YOW
1 stop9h 05m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 9/66:25 pm
YOW
- MDW
1 stop17h 35m
Multiple Airlines
Mon 9/143:20 pm
MDW
- YOW
1 stop15h 45m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$361
This Mytrip deal was found by Cheapflights users on 7/19. 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.
Wed 9/26:55 am
YOW
- ORD
1 stop11h 02m
Multiple Airlines
Wed 9/99:50 am
ORD
- YOW
1 stop13h 30m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$380
This FlightHub deal was found by Cheapflights users on 7/19. 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 8/1810:40 am
YOW
- MDW
1 stop4h 55m
Porter Airlines
Tue 8/253:15 pm
MDW
- YOW
1 stop5h 29m
Porter Airlines
Deal found 7/19![Porter Airlines logo]()
$394
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 8/206:55 am
YOW
- MDW
1 stop8h 40m
Multiple Airlines
Sun 8/233:15 pm
MDW
- YOW
1 stop8h 05m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$397
This Mytrip deal was found by Cheapflights users on 7/18. 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.
Tue 9/16:55 am
YOW
- ORD
1 stop13h 57m
Multiple Airlines
Sat 9/125:35 pm
ORD
- YOW
1 stop5h 45m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$400
This FlightHub deal was found by Cheapflights users on 7/18. 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
Fri 9/411:45 am
MDW
- YOW
1 stop8h 57m
Porter Airlines
Deal found 7/18![Porter Airlines logo]()
$404
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 8/106:25 pm
YOW
- MDW
1 stop16h 20m
Multiple Airlines
Fri 8/143:15 pm
MDW
- YOW
1 stop8h 05m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$409
This FlightHub deal was found by Cheapflights users on 7/19. 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 8/2110:40 am
YOW
- MDW
1 stop4h 55m
Porter Airlines
Sun 8/2310:20 am
MDW
- YOW
1 stop6h 34m
Porter Airlines
Deal found 7/19![Porter Airlines logo]()
$410
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 8/96:25 pm
YOW
- MDW
1 stop16h 20m
Multiple Airlines
Wed 8/123:15 pm
MDW
- YOW
1 stop8h 05m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 8/86:25 pm
YOW
- MDW
1 stop16h 15m
Multiple Airlines
Sat 8/1510:20 am
MDW
- YOW
1 stop13h 00m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$414
This American Airlines deal was found by Cheapflights users on 7/21. 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
Sun 9/138:03 am
ORD
- YOW
1 stop5h 52m
American Airlines
Deal found 7/21![American Airlines logo]()
$417
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 July 22, 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 July 22, 2026.
This Gotogate deal was found by Cheapflights users on 7/18. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/110:40 am
YOW
- MDW
1 stop4h 55m
Porter Airlines
Sat 9/1211:45 am
MDW
- YOW
1 stop6h 22m
Porter Airlines
Deal found 7/18![Porter Airlines logo]()
$477
This United Airlines deal was found by Cheapflights users on 7/21. 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 10/206:05 am
YOW
- ORD
1 stop11h 29m
United Airlines
Fri 10/239:35 pm
ORD
- YOW
1 stop18h 03m
United Airlines
Deal found 7/21![United Airlines logo]()
$607
This oojo deal was found by Cheapflights users on 7/21. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:55 am
YOW
- MDW
2 stops12h 38m
WestJet
Thu 8/276:42 pm
MDW
- YOW
2 stops21h 53m
WestJet
Deal found 7/21![WestJet logo]()
$670
This FlightHub deal was found by Cheapflights users on 7/18. 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 9/2410:40 am
YOW
- MDW
1 stop4h 55m
Porter Airlines
Sun 9/2711:45 am
MDW
- YOW
1 stop5h 07m
Porter Airlines
Deal found 7/18![Porter Airlines logo]()
$483
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 8/2110:40 am
YOW
- MDW
1 stop4h 55m
Porter Airlines
Fri 8/2810:25 am
MDW
- YOW
1 stop6h 29m
Porter Airlines
Deal found 7/22![Porter Airlines logo]()
$493
This United Airlines deal was found by Cheapflights users on 7/18. 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 stop11h 29m
United Airlines
Sat 9/55:00 am
ORD
- YOW
1 stop10h 38m
United Airlines
Deal found 7/18![United Airlines logo]()
$608
This FlightHub deal was found by Cheapflights users on 7/17. 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 8/1510:40 am
YOW
- MDW
1 stop24h 00m
Porter Airlines
Sat 8/2210:20 am
MDW
- YOW
1 stop25h 34m
Porter Airlines
Deal found 7/17![Porter Airlines logo]()
$515
This Trip.com deal was found by Cheapflights users on 7/20. 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 8/610:40 am
YOW
- MDW
1 stop4h 55m
Porter Airlines
Tue 8/1110:25 am
MDW
- YOW
1 stop6h 29m
Porter Airlines
Deal found 7/20![Porter Airlines logo]()
$517
This United Airlines deal was found by Cheapflights users on 7/17. 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 10/233:10 pm
YOW
- ORD
1 stop17h 32m
United Airlines
Sun 10/2510:57 am
ORD
- YOW
Nonstop2h 12m
United Airlines
Deal found 7/17![United Airlines logo]()
$673
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 8/83:30 pm
YOW
- MDW
1 stop19h 10m
Porter Airlines
Sun 8/93:15 pm
MDW
- YOW
1 stop5h 29m
Porter Airlines
Deal found 7/17![Porter Airlines logo]()
$537
This United Airlines deal was found by Cheapflights users on 7/21. 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.
Mon 9/76:25 am
YOW
- ORD
Nonstop2h 19m
United Airlines
Thu 9/106:21 pm
ORD
- YOW
Nonstop2h 14m
United Airlines
Deal found 7/21![United Airlines logo]()
$673
This United Airlines deal was found by Cheapflights users on 7/19. 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 10/245:20 pm
YOW
- ORD
Nonstop2h 26m
United Airlines
Wed 10/282:20 pm
ORD
- YOW
1 stop6h 36m
United Airlines
Deal found 7/19![United Airlines logo]()
$674
This Porter Airlines deal was found by Cheapflights users on 7/20. 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 10/2811:45 am
ORD
- YOW
1 stop5h 29m
Porter Airlines
Deal found 7/20![Porter Airlines logo]()
$568
This United Airlines deal was found by Cheapflights users on 7/18. 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 8/2610:37 am
YOW
- ORD
Nonstop2h 23m
United Airlines
Wed 9/210:40 am
ORD
- YOW
Nonstop2h 19m
United Airlines
Deal found 7/18![United Airlines logo]()
$677
This Mytrip deal was found by Cheapflights users on 7/20. 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 9/48:00 am
YOW
- MDW
1 stop4h 00m
Porter Airlines
Mon 9/711:45 am
MDW
- YOW
1 stop5h 07m
Porter Airlines
Deal found 7/20![Porter Airlines logo]()
$574
This KAYAK deal was found by Cheapflights users on 7/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1010:40 am
YOW
- MDW
1 stop24h 05m
Porter Airlines
Wed 8/1210:25 am
MDW
- YOW
1 stop6h 29m
Porter Airlines
Deal found 7/20![Porter Airlines logo]()
$627
This Porter Airlines deal was found by Cheapflights users on 7/18. 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.
Wed 8/268:30 am
YOW
- MDW
2 stops31h 05m
Porter Airlines
Fri 9/43:20 pm
MDW
- YOW
1 stop5h 22m
Porter Airlines
Deal found 7/18![Porter Airlines logo]()
$671
Last-minute flights from Ottawa to ChicagoDiscover last-minute flight deals from Ottawa to Chicago. Data last updated July 22, 2026 and is based on user searches.
Discover last-minute flight deals from Ottawa to Chicago. Data last updated July 22, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 8/86:25 pm
YOW
- MDW
1 stop16h 15m
Multiple Airlines
Sat 8/1510:20 am
MDW
- YOW
1 stop13h 00m
Multiple Airlines
Deal found 7/17![Multiple Airlines logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 8/86:25 pm
YOW
- MDW
1 stop16h 15m
Multiple Airlines
Tue 8/113:15 pm
MDW
- YOW
1 stop8h 05m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$418
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 8/96:25 pm
YOW
- MDW
1 stop16h 20m
Multiple Airlines
Wed 8/123:15 pm
MDW
- YOW
1 stop8h 05m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 8/106:25 pm
YOW
- MDW
1 stop16h 20m
Multiple Airlines
Fri 8/143:15 pm
MDW
- YOW
1 stop8h 05m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$409
This FlightHub deal was found by Cheapflights users on 7/18. 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.
Mon 8/1010:40 am
YOW
- MDW
1 stop4h 55m
Porter Airlines
Mon 8/1710:25 am
MDW
- YOW
1 stop6h 29m
Porter Airlines
Deal found 7/18![Porter Airlines logo]()
$419
This FlightHub deal was found by Cheapflights users on 7/19. 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 8/1810:40 am
YOW
- MDW
1 stop4h 55m
Porter Airlines
Tue 8/253:15 pm
MDW
- YOW
1 stop5h 29m
Porter Airlines
Deal found 7/19![Porter Airlines logo]()
$394
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 8/187:00 am
YOW
- ORD
2 stops30h 50m
Multiple Airlines
Tue 8/255:30 pm
ORD
- YOW
1 stop11h 05m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$425
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 8/206:55 am
YOW
- MDW
1 stop8h 40m
Multiple Airlines
Sun 8/233:15 pm
MDW
- YOW
1 stop8h 05m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$397
This Mytrip deal was found by Cheapflights users on 7/18. 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.
Thu 8/206:55 am
YOW
- ORD
1 stop11h 02m
Multiple Airlines
Sun 8/239:50 am
ORD
- YOW
1 stop13h 30m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$433
This FlightHub deal was found by Cheapflights users on 7/19. 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 8/2110:40 am
YOW
- MDW
1 stop4h 55m
Porter Airlines
Sun 8/2310:20 am
MDW
- YOW
1 stop6h 34m
Porter Airlines
Deal found 7/19![Porter Airlines logo]()
$410
This FlightHub deal was found by Cheapflights users on 7/18. 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
Fri 9/411:45 am
MDW
- YOW
1 stop8h 57m
Porter Airlines
Deal found 7/18![Porter Airlines logo]()
$404
This FlightHub deal was found by Cheapflights users on 7/20. 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
Tue 9/111:45 am
MDW
- YOW
1 stop5h 07m
Porter Airlines
Deal found 7/20![Porter Airlines logo]()
$439
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 July 22, 2026.
Search for one-way flight options from Ottawa to Chicago. Find affordable one-way fares based on user searches. Data last updated July 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 9/286:55 am
YOW
- MDW
1 stop8h 40m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 8/317:00 am
YOW
- ORD
1 stop30h 50m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 8/177:00 am
YOW
- ORD
1 stop30h 50m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 10/27:20 am
YOW
- ORD
1 stop10h 20m
WestJet
Deal found 7/22![WestJet logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 9/27:00 am
YOW
- ORD
2 stops30h 50m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$233
This American Airlines deal was found by Cheapflights users on 7/22. 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 9/18:40 am
YOW
- ORD
1 stop6h 40m
American Airlines
Deal found 7/22![American Airlines logo]()
$234
This American Airlines deal was found by Cheapflights users on 7/20. 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 9/108:40 am
YOW
- ORD
1 stop6h 40m
American Airlines
Deal found 7/20![American Airlines logo]()
$236
This FlightHub deal was found by Cheapflights users on 7/21. 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.
Mon 9/287:20 am
YOW
- ORD
1 stop10h 20m
WestJet
Deal found 7/21![WestJet logo]()
$239
This Mytrip deal was found by Cheapflights users on 7/22. 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.
Wed 9/166:25 pm
YOW
- ORD
2 stops21h 27m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$247
This Trip.com deal was found by Cheapflights users on 7/20. 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.
Wed 8/1910:40 am
YOW
- MDW
1 stop4h 55m
Porter Airlines
Deal found 7/20![Porter Airlines logo]()
$252
This American Airlines deal was found by Cheapflights users on 7/20. 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 8/198:40 am
YOW
- ORD
1 stop6h 40m
American Airlines
Deal found 7/20![American Airlines logo]()
$253
This Mytrip deal was found by Cheapflights users on 7/19. 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.
Thu 8/2010:40 am
YOW
- MDW
1 stop4h 55m
Porter Airlines
Deal found 7/19![Porter Airlines logo]()
$254
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 July 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $360 (Trip.com) |
One-way from | $193 (Kiwi.com) |
Popular in | January |
Cheapest in | February |
Average price | $612 |
Good round-trip deal | $539 or less |
Good one-way deal | $280 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 July 22, 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 9/1
10:40 am-2:35 pm
1 stop4h 55m
Chicago Midway
Sat 9/12
11:45 am-7:07 pm
1 stop6h 22m
$477
OttawaChicago
YOW - MDW
YOWMDW
Ottawa
Thu 9/24
10:40 am-2:35 pm
1 stop4h 55m
Chicago Midway
Sun 9/27
11:45 am-5:52 pm
1 stop5h 07m
$483
OttawaChicago
YOW - MDW
YOWMDW
Ottawa
Fri 8/21
10:40 am-2:35 pm
1 stop4h 55m
Chicago Midway
Fri 8/28
10:25 am-5:54 pm
1 stop6h 29m
$493
OttawaChicago
YOW - MDW
YOWMDW
Ottawa
Sat 8/15
10:40 am-9:40 am
1 stop24h 00m
Chicago Midway
Sat 8/22
10:20 am-12:54 pm
1 stop25h 34m
$515
OttawaChicago
YOW - MDW
YOWMDW
Ottawa
Thu 8/6
10:40 am-2:35 pm
1 stop4h 55m
Chicago Midway
Tue 8/11
10:25 am-5:54 pm
1 stop6h 29m
$517
OttawaChicago
YOW - MDW
YOWMDW
Ottawa
Sat 8/8
3:30 pm-9:40 am
1 stop19h 10m
Chicago Midway
Sun 8/9
3:15 pm-9:44 pm
1 stop5h 29m
$537
OttawaChicago
YOW - ORD
YOWORD
Ottawa
Sat 10/24
8:40 am-2:20 pm
1 stop6h 40m
Chicago O'Hare Intl
Wed 10/28
11:45 am-6:14 pm
1 stop5h 29m
$568
OttawaChicago
YOW - MDW
YOWMDW
Ottawa
Fri 9/4
8:00 am-11:00 am
1 stop4h 00m
Chicago Midway
Mon 9/7
11:45 am-5:52 pm
1 stop5h 07m
$574
OttawaChicago
YOW - ORD
YOWORD
Ottawa
Tue 10/20
6:05 am-4:34 pm
1 stop11h 29m
Chicago O'Hare Intl
Fri 10/23
9:35 pm-4:38 pm
1 stop18h 03m
$607
OttawaChicago
YOW - ORD
YOWORD
Ottawa
Wed 8/26
6:05 am-4:34 pm
1 stop11h 29m
Chicago O'Hare Intl
Sat 9/5
5:00 am-4:38 pm
1 stop10h 38m
$608
Showing 1-10 of 35 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 July.
| 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 July 22, 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 July 22, 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?
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 July 22, 2026.
Peruse reviews from past customers who have flown with Porter 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.
Food
7.5
Boarding
8.2
Entertainment
6.9
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodShannon,Jul 2026
YQT - YOW
Food
7.5
Boarding
8.2
Entertainment
6.9
Overall
8.0
Comfort
8.0
Crew
8.6
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
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Ottawa to Chicago
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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 July 22, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Ottawa to Chicago by cabin class
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Ottawa and Chicago flights
Browse other Ottawa and Chicago flight options. Last updated on July 22, 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 July 22, 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 July 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$324 | Average$661 | FlexibilityNo cancel fee | On-time69% |