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Cheap flights from Ottawa to Chicago from $171

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 10/7. 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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Find the cheapest flights from Ottawa to Chicago

Cheap round-trip flights

Logo
4:25 pm - 10:21 amYOW-MDW
18h 56m1 stop
Logo
8:05 am - 5:20 pmMDW-YOW
32h 15m2 stops
$340
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Fri, Oct 3 - Wed, Oct 15
United Airlines Logo
6:33 am - 8:00 amYOW-ORD
2h 27mnonstop
United Airlines Logo
8:50 am - 2:13 pmORD-YOW
4h 23m1 stop
$341United Airlines
Find Deal
Fri, Oct 3 - Wed, Oct 15
Logo
1:25 pm - 4:24 pmYOW-MDW
3h 59m1 stop
Logo
9:35 am - 12:22 amMDW-YOW
13h 47m1 stop
$342
Find Deal
Wed, Oct 1 - Sat, Oct 11
United Airlines Logo
7:29 pm - 11:15 pmYOW-ORD
4h 46m1 stop
United Airlines Logo
8:50 am - 2:13 pmORD-YOW
4h 23m1 stop
$347United Airlines
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Fri, Oct 3 - Wed, Oct 15
WestJet Logo
12:20 pm - 12:39 pmYOW-ORD
25h 19m2 stops
WestJet Logo
5:30 pm - 4:19 pmORD-YOW
21h 49m2 stops
$373WestJet
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Fri, Oct 3 - Mon, Oct 6
Porter Airlines Logo
9:35 am - 4:24 pmYOW-MDW
7h 49m1 stop
Porter Airlines Logo
9:35 am - 4:34 pmMDW-YOW
5h 59m1 stop
$384Porter Airlines
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Thu, Oct 9 - Sun, Oct 12
WestJet Logo
5:40 am - 4:11 pmYOW-ORD
11h 31m2 stops
WestJet Logo
11:14 am - 12:42 amORD-YOW
12h 28m2 stops
$399WestJet
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Fri, Nov 7 - Mon, Nov 10
Porter Airlines Logo
12:10 pm - 3:20 pmYOW-MDW
4h 10m1 stop
Porter Airlines Logo
4:15 pm - 10:29 pmMDW-YOW
5h 14m1 stop
$466Porter Airlines
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Mon, Nov 10 - Sun, Nov 16
Air Canada Logo
10:50 am - 2:55 pmYOW-ORD
5h 05m1 stop
Air Canada Logo
7:15 am - 12:22 pmORD-YOW
4h 07m1 stop
$513Air Canada
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Mon, Nov 10 - Sun, Nov 16
Lufthansa Logo
6:20 am - 8:05 amYOW-ORD
2h 45mnonstop
Lufthansa Logo
6:00 pm - 9:18 pmORD-YOW
2h 18mnonstop
$528Lufthansa
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Thu, Jan 8 - Sun, Jan 11

United Airlines flights from Ottawa to Chicago

Our best United Airlines deals on Ottawa to Chicago flight tickets
United Airlines
Oct 3
YOW6:33 amOttawa
2h 27m
ORD8:00 amChicago O'Hare Intl
Oct 15
ORD8:50 amChicago O'Hare Intl
4h 23m
1 stop
YOW2:13 pmOttawa
$341
Find similar
United Airlines
Oct 3
YOW7:29 pmOttawa
4h 46m
1 stop
ORD11:15 pmChicago O'Hare Intl
Oct 15
ORD8:50 amChicago O'Hare Intl
4h 23m
1 stop
YOW2:13 pmOttawa
$347
Find similar
United Airlines
Oct 11
YOW2:48 pmOttawa
6h 26m
1 stop
ORD8:14 pmChicago O'Hare Intl
Oct 13
ORD10:45 amChicago O'Hare Intl
9h 24m
2 stops
YOW9:09 pmOttawa
$406
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WestJet flights from Ottawa to Chicago

Our best WestJet deals on Ottawa to Chicago flight tickets
WestJet
Oct 3
YOW12:20 pmOttawa
25h 19m
2 stops
ORD12:39 pmChicago O'Hare Intl
Oct 6
ORD5:30 pmChicago O'Hare Intl
21h 49m
2 stops
YOW4:19 pmOttawa
$373
Find similar
WestJet
Nov 7
YOW5:40 amOttawa
11h 31m
2 stops
ORD4:11 pmChicago O'Hare Intl
Nov 10
ORD11:14 amChicago O'Hare Intl
12h 28m
2 stops
YOW12:42 amOttawa
$399
Find similar
WestJet
Dec 2
YOW5:40 amOttawa
11h 38m
2 stops
ORD4:18 pmChicago O'Hare Intl
Dec 4
ORD11:15 amChicago O'Hare Intl
12h 27m
2 stops
YOW12:42 amOttawa
$412
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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 September 15, 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

Fri 10/3

4:25 pm-10:21 am

1 stop18h 56m

Chicago Midway

Wed 10/15

8:05 am-5:20 pm

2 stops32h 15m

$340

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 10/3

6:33 am-8:00 am

Nonstop2h 27m

Chicago O'Hare Intl

Wed 10/15

8:50 am-2:13 pm

1 stop4h 23m

$341

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 10/1

1:25 pm-4:24 pm

1 stop3h 59m

Chicago Midway

Sat 10/11

9:35 am-12:22 am

1 stop13h 47m

$342

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 10/3

7:29 pm-11:15 pm

1 stop4h 46m

Chicago O'Hare Intl

Wed 10/15

8:50 am-2:13 pm

1 stop4h 23m

$347

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 10/3

12:20 pm-12:39 pm

2 stops25h 19m

Chicago O'Hare Intl

Mon 10/6

5:30 pm-4:19 pm

2 stops21h 49m

$373

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 10/9

9:35 am-4:24 pm

1 stop7h 49m

Chicago Midway

Sun 10/12

9:35 am-4:34 pm

1 stop5h 59m

$384

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 11/7

5:40 am-4:11 pm

2 stops11h 31m

Chicago O'Hare Intl

Mon 11/10

11:14 am-12:42 am

2 stops12h 28m

$399

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 11/10

12:10 pm-3:20 pm

1 stop4h 10m

Chicago Midway

Sun 11/16

4:15 pm-10:29 pm

1 stop5h 14m

$466

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Mon 11/10

10:50 am-2:55 pm

1 stop5h 05m

Chicago O'Hare Intl

Sun 11/16

7:15 am-12:22 pm

1 stop4h 07m

$513

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Thu 1/8

6:20 am-8:05 am

Nonstop2h 45m

Chicago O'Hare Intl

Sun 1/11

6:00 pm-9:18 pm

Nonstop2h 18m

$528

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 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 $338. 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 $505. 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 $661.

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 $653.

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 $516 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?

You could potentially save up to 71% on your flight if you consider stops on a Ottawa to Chicago flight.

How have Ottawa to Chicago flight prices changed over time?

As of September 2025, prices for Ottawa to Chicago flights are approximately 9% more expensive 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

$382

Fastest flight time

2h 24m

Direct flights

Tue, Wed, Thu, Fri, Sat and Sun

Airports in Chicago

1 airport
The best one-way flight to Chicago from Ottawa in the past 72 hours is $382. The best round-trip flight deal from Ottawa to Chicago found on momondo in the last 72 hours is $580.
The fastest flight from Ottawa to Chicago takes 2h 24m
Direct flights go from Ottawa to Chicago on Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
Search flight deals

  • How far is Ottawa to Chicago by plane?

    The straight-line distance from Ottawa to Chicago is 643.5 mi. 2h 27m 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
United AirlinesPriceFrom $324Free CancellationRating
7.4
8,929 reviews
Search United Airlines flights
Air CanadaPriceFrom $326Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights

  • United Airlines Flights From Ottawa to Chicago

    The lowest priced United Airlines flight from Ottawa to Chicago from the last 72 hours was $324. Generally, United Airlines has 21 flights on this route every week with an average price of $519. 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 10,000 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
Lansing
Portage
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