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Cheap flights from Ottawa to Chicago from $165

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Ottawa to Chicago departing on 9/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Porter Airlines Logo
1:25 pm - 4:24 pmYOW-MDW
3h 59m1 stop
Porter Airlines Logo
9:35 am - 4:34 pmMDW-YOW
5h 59m1 stop
$286Porter Airlines
Find Deal
Tue, Sep 2 - Thu, Sep 11
Porter Airlines Logo
1:25 pm - 4:24 pmYOW-MDW
3h 59m1 stop
Porter Airlines Logo
9:35 am - 4:34 pmMDW-YOW
5h 59m1 stop
$291Porter Airlines
Find Deal
Fri, Sep 12 - Mon, Sep 15
WestJet Logo
7:50 am - 4:43 pmYOW-ORD
9h 53m1 stop
WestJet Logo
2:20 pm - 12:45 amORD-YOW
9h 25m1 stop
$310WestJet
Find Deal
Fri, Oct 24 - Sun, Oct 26
United Airlines Logo
5:25 pm - 6:54 pmYOW-ORD
2h 29mnonstop
United Airlines Logo
10:50 am - 2:04 pmORD-YOW
2h 14mnonstop
$323United Airlines
Find Deal
Fri, Sep 12 - Mon, Sep 15
United Airlines Logo
6:33 am - 8:00 amYOW-ORD
2h 27mnonstop
United Airlines Logo
10:50 am - 2:04 pmORD-YOW
2h 14mnonstop
$324United Airlines
Find Deal
Wed, Sep 3 - Sun, Sep 7
WestJet Logo
6:00 am - 4:43 pmYOW-ORD
11h 43m1 stop
WestJet Logo
5:30 pm - 12:40 amORD-YOW
30h 10m1 stop
$328WestJet
Find Deal
Fri, Sep 26 - Sun, Sep 28
Air Canada Logo
6:00 am - 9:51 amYOW-ORD
4h 51m1 stop
Air Canada Logo
8:25 pm - 1:34 amORD-YOW
4h 09m1 stop
$340Air Canada
Find Deal
Wed, Sep 3 - Sun, Sep 7
Logo
3:50 pm - 11:59 pmYOW-ORD
9h 09m1 stop
Logo
6:56 am - 5:06 pmORD-YOW
9h 10m1 stop
$352
Find Deal
Sat, Aug 23 - Wed, Aug 27
Logo
3:50 pm - 11:59 pmYOW-ORD
9h 09m1 stop
Logo
6:56 am - 4:57 pmORD-YOW
9h 01m1 stop
$356
Find Deal
Sat, Aug 30 - Tue, Sep 2
Air Canada Logo
8:35 am - 1:13 pmYOW-ORD
5h 38m1 stop
Air Canada Logo
9:55 am - 5:04 pmORD-YOW
6h 09m1 stop
$420Air Canada
Find Deal
Fri, Aug 29 - Tue, Sep 2

United Airlines flights from Ottawa to Chicago

Our best United Airlines deals on Ottawa to Chicago flight tickets
United Airlines
Sep 12
YOW5:25 pmOttawa
2h 29m
ORD6:54 pmChicago O'Hare Intl
Sep 15
ORD10:50 amChicago O'Hare Intl
2h 14m
YOW2:04 pmOttawa
$323
Find similar
United Airlines
Sep 3
YOW6:33 amOttawa
2h 27m
ORD8:00 amChicago O'Hare Intl
Sep 7
ORD10:50 amChicago O'Hare Intl
2h 14m
YOW2:04 pmOttawa
$324
Find similar
United Airlines
Sep 13
YOW6:33 amOttawa
2h 27m
ORD8:00 amChicago O'Hare Intl
Sep 14
ORD1:55 pmChicago O'Hare Intl
2h 11m
YOW5:06 pmOttawa
$327
Find similar

Air Canada flights from Ottawa to Chicago

Our best Air Canada deals on Ottawa to Chicago flight tickets
Air Canada
Sep 3
YOW6:00 amOttawa
4h 51m
1 stop
ORD9:51 amChicago O'Hare Intl
Sep 7
ORD8:25 pmChicago O'Hare Intl
4h 09m
1 stop
YOW1:34 amOttawa
$340
Find similar
Air Canada
Aug 29
YOW8:35 amOttawa
5h 38m
1 stop
ORD1:13 pmChicago O'Hare Intl
Sep 2
ORD9:55 amChicago O'Hare Intl
6h 09m
1 stop
YOW5:04 pmOttawa
$420
Find similar
Air Canada
Aug 29
YOW5:15 amOttawa
4h 54m
1 stop
ORD9:09 amChicago O'Hare Intl
Sep 2
ORD8:25 pmChicago O'Hare Intl
4h 09m
1 stop
YOW1:34 amOttawa
$421
Find similar

momondo 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, momondo users made 832,500 searches. Data last updated August 2, 2025.
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

Price

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 9/2

1:25 pm-4:24 pm

1 stop3h 59m

Chicago Midway

Thu 9/11

9:35 am-4:34 pm

1 stop5h 59m

$286

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 9/12

1:25 pm-4:24 pm

1 stop3h 59m

Chicago Midway

Mon 9/15

9:35 am-4:34 pm

1 stop5h 59m

$291

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 10/24

7:50 am-4:43 pm

1 stop9h 53m

Chicago O'Hare Intl

Sun 10/26

2:20 pm-12:45 am

1 stop9h 25m

$310

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 9/12

5:25 pm-6:54 pm

Nonstop2h 29m

Chicago O'Hare Intl

Mon 9/15

10:50 am-2:04 pm

Nonstop2h 14m

$323

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Wed 9/3

6:33 am-8:00 am

Nonstop2h 27m

Chicago O'Hare Intl

Sun 9/7

10:50 am-2:04 pm

Nonstop2h 14m

$324

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 9/26

6:00 am-4:43 pm

1 stop11h 43m

Chicago O'Hare Intl

Sun 9/28

5:30 pm-12:40 am

1 stop30h 10m

$328

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Wed 9/3

6:00 am-9:51 am

1 stop4h 51m

Chicago O'Hare Intl

Sun 9/7

8:25 pm-1:34 am

1 stop4h 09m

$340

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Sat 8/23

3:50 pm-11:59 pm

1 stop9h 09m

Chicago O'Hare Intl

Wed 8/27

6:56 am-5:06 pm

1 stop9h 10m

$352

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Sat 8/30

3:50 pm-11:59 pm

1 stop9h 09m

Chicago O'Hare Intl

Tue 9/2

6:56 am-4:57 pm

1 stop9h 01m

$356

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 8/29

8:35 am-1:13 pm

1 stop5h 38m

Chicago O'Hare Intl

Tue 9/2

9:55 am-5:04 pm

1 stop6h 09m

$420

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Ottawa to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Ottawa and Chicago?

What is the cheapest month to fly to Chicago?

The month of May is, on average, the cheapest month to fly to Chicago from Ottawa, with most prices found around $339. If you’re not able to fly to Chicago in May, then June is your next best option. Flight prices from Ottawa to Chicago during June average around $358.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $464. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Ottawa to Chicago for around $681.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Ottawa to Chicago during this time can be as low as $353. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $654.

What is the cheapest Ottawa to Chicago flight route?

Fly from Ottawa to Chicago O'Hare Intl for the best Ottawa - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Ottawa when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $509 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Ottawa for as low as $232 on momondo.

What cabin class options are available on Ottawa to Chicago flights?

There are 4 cabin classes available to choose from on Ottawa to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Ottawa to Chicago flights?

No. A direct flight is the cheapest option for a flight between Ottawa to Chicago.

How have Ottawa to Chicago flight prices changed over time?

As of August 2025, prices for Ottawa to Chicago flights are approximately 7% cheaper when compared to flights at the same time last year.

When to book flights from Ottawa to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Ottawa to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Ottawa to Chicago (YOW to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Ottawa to Chicago

Best Price Found

$165

Fastest flight time

2h 22m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Ottawa in the past 72 hours is $165. The best round-trip flight deal from Ottawa to Chicago found on momondo in the last 72 hours is $286.
The fastest flight from Ottawa to Chicago takes 2h 22m
Direct flights go from Ottawa to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

  • How far is Ottawa to Chicago by plane?

    The straight-line distance from Ottawa to Chicago is 643.5 mi. 2h 24m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Ottawa Airport to Chicago?

    Prices for flights from Ottawa Airport to Chicago were last updated today.

  • How many operators does momondo search for flights from Ottawa Airport to Chicago?

  • How old do you have to be to fly from Ottawa Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Ottawa Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Ottawa to Chicago?

  • What is the most popular airline from Ottawa to Chicago?

Best airlines flying from Ottawa to Chicago

Compare and see reviews for airlines that fly from Ottawa to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom $326Free CancellationRating
7.1
9,855 reviews
Search Air Canada flights
United AirlinesPriceFrom $376Free CancellationRating
7.4
8,904 reviews
Search United Airlines flights

  • United Airlines Flights From Ottawa to Chicago

    The lowest priced United Airlines flight from Ottawa to Chicago from the last 72 hours was $376. Generally, United Airlines has 21 flights on this route every week with an average price of $547. United Airlines is rated 7.4/10 by our users.

  • Air Canada Flights From Ottawa to Chicago

    $326 is the best Air Canada flight deal from Ottawa to Chicago found on momondo over the last 72 hours. The average Air Canada ticket price found was closer to $554, however, with flight time and availability significantly affecting the price. Air Canada (7.1/10 from 9,855 user reviews) flies into Chicago from Ottawa 21 times in an average week so prices can vary.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Ottawa to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Ottawa to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Ottawa to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Ottawa to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Ottawa to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Ottawa.

I’m not ready to book a flight from Ottawa to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Ottawa to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport