background

Flight Deals from Ottawa to Chicago from $239

Bundle + Save

Bundle + Save

Top flight deals from leading airlines:

UA LogoAC LogoQR LogoSQ LogoNH LogoEK LogoJL Logo

... and +100s more

Incredible Deals

Save up to 50% on select flights with Priceline

Bundle & Save

Save an average of $240 per person when bundling your flight and hotel together with Priceline

Best Price Guarantee

If a VIP member finds a better price elsewhere, we'll refund up to 200% of the difference

Help 24/7

We’re always here for you - reach us 24 hours a day, 7 days a week

Stops

  • Up to 2 stops
    $527
  • Up to 3 stops
    $800
  • Up to 1 stop
    $670

Airlines

  • Air Canada
    $527
  • American Airlines
    $614
  • Porter Airlines
    $549
  • United Airlines
    $647

Cabin Class

  • Economy
    $527

Departure Airports

  • Ottawa Macdonald-Cartier International Airport
    $527

Arrival Airports

  • Chicago Metropolitan Area
    $527

Layover Airports

  • Chicago Midway Airport
    $549
  • Chicago O Hare Airport
    $527
  • Newark Liberty Airport
    $647
  • Ottawa Macdonald-Cartier International Airport
    $527
  • Reagan Washington National Airport
    $800
  • Toronto Island Airport
    $527
  • Toronto Pearson Airport
    $587
  • Washington Dulles Airport
    $681

Best Price. GUARANTEED.

Exclusively for Priceline Members
Tired of searching? Book now!
We'll refund the difference if you find a lower price.

Air Canada Logo
Air Canada

06/13/26

YOW
3h 15m
YTZ
ORD

06/13/26

CHI
Air Canada Logo
Air Canada

06/15/26

CHI
5h 51m
YTZ
YOW

06/15/26

YOW
$527
Air Canada Logo
Air Canada

06/18/26

YOW
3h 15m
YTZ
ORD

06/18/26

CHI
Air Canada Logo
Air Canada

06/21/26

CHI
5h 52m
YTZ
YOW

06/21/26

YOW
$541
Porter Airlines Logo
Porter Airlines

06/08/26

YOW
3h 35m
YTZ
MDW

06/08/26

CHI
Porter Airlines Logo
Porter Airlines

06/12/26

CHI
4h 44m
YTZ
YOW

06/12/26

YOW
$549
Bundle + Save
Book a flight & hotel together for extra savings.
On average save $240 per traveler
Air Canada Logo
Air Canada

06/08/26

YOW
3h 15m
YTZ
ORD

06/08/26

CHI
Air Canada Logo
Air Canada

06/12/26

CHI
5h 51m
YTZ
YOW

06/12/26

YOW
$553
Porter Airlines Logo
Porter Airlines

06/19/26

YOW
3h 35m
YTZ
MDW

06/19/26

CHI
Porter Airlines Logo
Porter Airlines

06/28/26

CHI
7h 29m
YTZ
YOW

06/28/26

YOW
$582
Air Canada Logo
Air Canada

05/31/26

YOW
3h 25m
YYZ
ORD

05/31/26

CHI
Air Canada Logo
Air Canada

06/06/26

CHI
5h 51m
YTZ
YOW

06/06/26

YOW
$587
Porter Airlines Logo
Porter Airlines

06/03/26

YOW
5h 37m
YYZ
ORD

06/03/26

CHI
Porter Airlines Logo
Porter Airlines

06/05/26

CHI
4h 39m
YTZ
YOW

06/05/26

YOW
$593
Porter Airlines Logo
Porter Airlines

06/13/26

YOW
5h 40m
YYZ
ORD

06/13/26

CHI
Porter Airlines Logo
Porter Airlines

06/15/26

CHI
4h 44m
YTZ
YOW

06/15/26

YOW
$593
Porter Airlines Logo
Porter Airlines

06/04/26

YOW
5h 44m
YYZ
ORD

06/04/26

CHI
Porter Airlines Logo
Porter Airlines

06/09/26

CHI
4h 39m
YTZ
YOW

06/09/26

YOW
$595
Porter Airlines Logo
Porter Airlines

06/06/26

YOW
5h 40m
YYZ
ORD

06/06/26

CHI
Porter Airlines Logo
Porter Airlines

06/12/26

CHI
4h 44m
YTZ
YOW

06/12/26

YOW
$595
American Airlines Logo
American Airlines

05/31/26

YOW
5h 37m
YYZ
ORD

05/31/26

CHI
American Airlines Logo
American Airlines

06/06/26

CHI
9h 33m
YYZ
YOW

06/07/26

YOW
$614
Air Canada Logo
Air Canada

06/13/26

YOW
3h 15m
YTZ
ORD

06/13/26

CHI
Air Canada Logo
Air Canada

06/15/26

CHI
3h 13m
YOW

06/15/26

YOW
$627
United Airlines Logo
United Airlines

06/05/26

YOW
8h 20m
EWR
ORD

06/05/26

CHI
United Airlines Logo
United Airlines

06/08/26

CHI
9h 54m
EWR
YOW

06/08/26

YOW
$647
Bundle + Save
Book a flight & hotel together for extra savings.
On average save $240 per traveler
United Airlines Logo
United Airlines

06/19/26

YOW
1h 20m
ORD

06/19/26

CHI
United Airlines Logo
United Airlines

06/23/26

CHI
3h 13m
YOW

06/23/26

YOW
$670
United Airlines Logo
United Airlines

06/16/26

YOW
1h 20m
ORD

06/16/26

CHI
United Airlines Logo
United Airlines

06/19/26

CHI
3h 12m
YOW

06/19/26

YOW
$671
United Airlines Logo
United Airlines

06/10/26

YOW
1h 20m
ORD

06/10/26

CHI
United Airlines Logo
United Airlines

06/16/26

CHI
3h 13m
YOW

06/16/26

YOW
$671
United Airlines Logo
United Airlines

06/11/26

YOW
1h 20m
ORD

06/11/26

CHI
United Airlines Logo
United Airlines

06/14/26

CHI
3h 12m
YOW

06/14/26

YOW
$671
United Airlines Logo
United Airlines

06/13/26

YOW
1h 20m
ORD

06/13/26

CHI
United Airlines Logo
United Airlines

06/15/26

CHI
3h 12m
YOW

06/15/26

YOW
$671
United Airlines Logo
United Airlines

06/16/26

YOW
1h 20m
ORD

06/16/26

CHI
United Airlines Logo
United Airlines

06/19/26

CHI
5h 42m
IAD
YOW

06/19/26

YOW
$681
United Airlines Logo
United Airlines

06/13/26

YOW
3h 56m
IAD
ORD

06/13/26

CHI
United Airlines Logo
United Airlines

06/15/26

CHI
5h 51m
YTZ
YOW

06/15/26

YOW
$692
United Airlines Logo
United Airlines

06/16/26

YOW
3h 56m
IAD
ORD

06/16/26

CHI
United Airlines Logo
United Airlines

06/19/26

CHI
5h 42m
IAD
YOW

06/19/26

YOW
$696
United Airlines Logo
United Airlines

06/05/26

YOW
8h 20m
EWR
ORD

06/05/26

CHI
United Airlines Logo
United Airlines

06/08/26

CHI
3h 12m
YOW

06/08/26

YOW
$701
Porter Airlines Logo
Porter Airlines

06/21/26

YOW
3h 35m
YTZ
MDW

06/21/26

CHI
Porter Airlines Logo
Porter Airlines

06/21/26

CHI
11h 30m
YYZ
YOW

06/22/26

YOW
$730
Bundle + Save
Book a flight & hotel together for extra savings.
On average save $240 per traveler
United Airlines Logo
United Airlines

06/16/26

YOW
7h 26m
YYZ
IAD
ORD

06/16/26

CHI
United Airlines Logo
United Airlines

06/19/26

CHI
5h 11m
DCA
YOW

06/19/26

YOW
$800
United Airlines Logo
United Airlines

06/01/26

YOW
3h 53m
DCA
ORD

06/01/26

CHI
United Airlines Logo
United Airlines

06/05/26

CHI
3h 13m
YOW

06/05/26

YOW
$810
American Airlines Logo
American Airlines

06/13/26

YOW
5h 40m
YYZ
ORD

06/13/26

CHI
American Airlines Logo
American Airlines

06/15/26

CHI
6h 47m
YYZ
YOW

06/15/26

YOW
$817
American Airlines Logo
American Airlines

06/19/26

YOW
5h 40m
YYZ
ORD

06/19/26

CHI
American Airlines Logo
American Airlines

06/28/26

CHI
6h 47m
YYZ
YOW

06/28/26

YOW
$838
United Airlines Logo
United Airlines

06/16/26

YOW
7h 26m
YYZ
IAD
ORD

06/16/26

CHI
United Airlines Logo
United Airlines

06/19/26

CHI
10h 24m
EWR
IAD
YOW

06/19/26

YOW
$924
American Airlines Logo
American Airlines

06/18/26

YOW
5h 44m
YYZ
ORD

06/18/26

CHI
American Airlines Logo
American Airlines

06/21/26

CHI
6h 47m
YYZ
YOW

06/21/26

YOW
$1139
American Airlines Logo
American Airlines

06/08/26

YOW
5h 40m
YYZ
ORD

06/08/26

CHI
American Airlines Logo
American Airlines

06/12/26

CHI
8h 20m
YYZ
YOW

06/12/26

YOW
$1148

Top Deals on flights from Ottawa to Chicago

Ottawa, CA (YOW) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jun 1

YOW
6h 37m
YYZ

Jun 1

ORD

as low as

$239

Ottawa, CA (YOW) - Chicago, US (CHI)

Air Canada Logo
Air Canada

Jun 5

YOW
4h 15m
YTZ

Jun 5

ORD

as low as

$298

Ottawa, CA (YOW) - Chicago, US (CHI)

Porter Airlines Logo
Porter Airlines

Jun 4

YOW
4h 35m
YTZ

Jun 4

MDW

as low as

$301

Ottawa, CA (YOW) - Chicago, US (CHI)

United Airlines Logo
United Airlines

May 27

YOW
9h 20m
EWR

May 27

ORD

as low as

$332

Ottawa, CA (YOW) - Chicago, US (CHI)

 Logo

Jun 5

YOW
10h 20m
YYC

Jun 5

ORD

as low as

$370

Good to Know

Essential information to help you plan your flight from Ottawa to Chicago

Cheapest Flight

$239

The lowest price we found in the last two weeks, departing Jun 1 and returning Jun 1

Airline AA1 stop ‧ 6h 37m ‧ economy

Fastest Flights

$670

The fastest flight that we found in the last two weeks, departing Jun 19 and returning Jun 23

Airline UA1 stop ‧ 1h 20m ‧ economy

Cheapest Flight Round-trip

$527

Cheapest price found in the last 14 days, departing Jun 13 and returning Jun 15

Airline AC2 stops ‧ 3h 15m ‧ economy

Cheapest Flight One-way

$239

Cheapest price found in the last 14 days, departing Jun 1

Airline AA1 stop ‧ 6h 37m ‧ economy

Cheapest Layover airport

$239

The cheapest layover airport to Chicago is currently $239

Airline AA1 stop ‧ 6h 37m ‧ economy

Best Arrival airport

$301

The best arrival airport to Chicago is currently $301

Airline PD1 stop ‧ 4h 35m ‧ economy

Best Departure airport

$301

The best departure airport to Chicago is currently $301

Airline PD1 stop ‧ 4h 35m ‧ economy

Cheapest Airline

$301

The cheapest airline to Chicago is currently $301

Airline PD1 stop ‧ 4h 35m ‧ economy

Flights to Chicago