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Cheap flights from Hamilton, Ontario to Chicago from C$ 239

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Hamilton, Ontario to Chicago departing on 27/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Hamilton, Ontario to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:25 a.m. - 12:24 a.m.
YHM
-
ORD
17h 59m
1 stop
Multiple Airlines Logo
5:05 a.m. - 3:00 p.m.
ORD
-
YHM
8h 55m
1 stop
C$ 505Multiple Airlines
Thu, 23 Apr - Thu, 30 Apr
Multiple Airlines Logo
7:25 a.m. - 6:20 p.m.
YHM
-
ORD
11h 55m
2 stops
Multiple Airlines Logo
5:05 a.m. - 3:00 p.m.
ORD
-
YHM
8h 55m
1 stop
C$ 543Multiple Airlines
Thu, 23 Apr - Thu, 30 Apr
Multiple Airlines Logo
8:15 a.m. - 12:27 a.m.
YHM
-
ORD
17h 12m
1 stop
Multiple Airlines Logo
5:05 a.m. - 3:55 p.m.
ORD
-
YHM
9h 50m
1 stop
C$ 621Multiple Airlines
Mon, 4 May - Sat, 9 May
Multiple Airlines Logo
6:10 p.m. - 11:33 a.m.
YHM
-
ORD
18h 23m
2 stops
Multiple Airlines Logo
7:45 p.m. - 3:55 p.m.
ORD
-
YHM
19h 10m
1 stop
C$ 652Multiple Airlines
Fri, 1 May - Fri, 8 May
Multiple Airlines Logo
8:15 a.m. - 12:24 a.m.
YHM
-
ORD
17h 09m
1 stop
Multiple Airlines Logo
5:05 a.m. - 3:55 p.m.
ORD
-
YHM
9h 50m
1 stop
C$ 671Multiple Airlines
Sat, 2 May - Sat, 9 May
Multiple Airlines Logo
7:25 a.m. - 9:17 p.m.
YHM
-
ORD
14h 52m
1 stop
Multiple Airlines Logo
5:05 a.m. - 3:00 p.m.
ORD
-
YHM
8h 55m
1 stop
C$ 704Multiple Airlines
Thu, 16 Apr - Thu, 23 Apr
Multiple Airlines Logo
8:15 a.m. - 11:07 p.m.
YHM
-
ORD
15h 52m
2 stops
Multiple Airlines Logo
5:05 a.m. - 3:55 p.m.
ORD
-
YHM
9h 50m
1 stop
C$ 716Multiple Airlines
Sat, 2 May - Sat, 9 May
Multiple Airlines Logo
7:25 a.m. - 10:23 a.m.
YHM
-
ORD
27h 58m
2 stops
Multiple Airlines Logo
5:05 a.m. - 3:00 p.m.
ORD
-
YHM
8h 55m
1 stop
C$ 741Multiple Airlines
Thu, 16 Apr - Thu, 23 Apr
Multiple Airlines Logo
7:00 a.m. - 11:33 a.m.
YHM
-
ORD
29h 33m
2 stops
Multiple Airlines Logo
1:43 p.m. - 3:00 p.m.
ORD
-
YHM
24h 17m
1 stop
C$ 782Multiple Airlines
Fri, 17 Apr - Fri, 24 Apr
Multiple Airlines Logo
7:00 a.m. - 10:54 a.m.
YHM
-
ORD
28h 54m
2 stops
Multiple Airlines Logo
5:05 a.m. - 3:00 p.m.
ORD
-
YHM
8h 55m
1 stop
C$ 792Multiple Airlines
Sun, 5 Apr - Thu, 23 Apr

WestJet flights from Hamilton, Ontario to Chicago

Our best WestJet deals on Hamilton, Ontario to Chicago flight tickets
WestJet
26 Apr
YHM6:10 p.m.Hamilton
23h 30m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
30 Apr
ORD5:30 p.m.Chicago O'Hare Intl
22h 45m
1 stop
YHM5:15 p.m.Hamilton
C$ 1,218
WestJet
23 Apr
YHM6:10 p.m.Hamilton
20h 25m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
30 Apr
ORD5:30 p.m.Chicago O'Hare Intl
22h 45m
1 stop
YHM5:15 p.m.Hamilton
C$ 1,246
WestJet
26 Apr
YHM6:10 p.m.Hamilton
23h 30m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
1 May
ORD5:30 p.m.Chicago O'Hare Intl
22h 45m
1 stop
YHM5:15 p.m.Hamilton
C$ 1,366

momondo Fare Finder

 
Customize your flight search to find flights from Hamilton, Ontario 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 96,600 searches. Data last updated 22 March 2026.
Use the filters below to find and compare flights from Hamilton, Ontario to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 23/4

7:25 a.m.-12:24 a.m.

1 stop17h 59m

Chicago O'Hare Intl

Thu 30/4

5:05 a.m.-3:00 p.m.

1 stop8h 55m

C$ 505
Quickest round-trip

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 23/4

7:25 a.m.-6:20 p.m.

2 stops11h 55m

Chicago O'Hare Intl

Thu 30/4

5:05 a.m.-3:00 p.m.

1 stop8h 55m

C$ 543

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Mon 4/5

8:15 a.m.-12:27 a.m.

1 stop17h 12m

Chicago O'Hare Intl

Sat 9/5

5:05 a.m.-3:55 p.m.

1 stop9h 50m

C$ 621

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 1/5

6:10 p.m.-11:33 a.m.

2 stops18h 23m

Chicago O'Hare Intl

Fri 8/5

7:45 p.m.-3:55 p.m.

1 stop19h 10m

C$ 652

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sat 2/5

8:15 a.m.-12:24 a.m.

1 stop17h 09m

Chicago O'Hare Intl

Sat 9/5

5:05 a.m.-3:55 p.m.

1 stop9h 50m

C$ 671

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 16/4

7:25 a.m.-9:17 p.m.

1 stop14h 52m

Chicago O'Hare Intl

Thu 23/4

5:05 a.m.-3:00 p.m.

1 stop8h 55m

C$ 704

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sat 2/5

8:15 a.m.-11:07 p.m.

2 stops15h 52m

Chicago O'Hare Intl

Sat 9/5

5:05 a.m.-3:55 p.m.

1 stop9h 50m

C$ 716

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 16/4

7:25 a.m.-10:23 a.m.

2 stops27h 58m

Chicago O'Hare Intl

Thu 23/4

5:05 a.m.-3:00 p.m.

1 stop8h 55m

C$ 741

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 17/4

7:00 a.m.-11:33 a.m.

2 stops29h 33m

Chicago O'Hare Intl

Fri 24/4

1:43 p.m.-3:00 p.m.

1 stop24h 17m

C$ 782

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sun 5/4

7:00 a.m.-10:54 a.m.

2 stops28h 54m

Chicago O'Hare Intl

Thu 23/4

5:05 a.m.-3:00 p.m.

1 stop8h 55m

C$ 792

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 Hamilton, Ontario 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 day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 579. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 1,020. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

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

In the morning is the cheapest time of day to fly from Hamilton, Ontario to Chicago when you can find flight prices for as low as C$ 657. Flying to Chicago in the morning is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,088 per ticket.

When to book flights from Hamilton, Ontario to Chicago

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

Cheap Hamilton, Ontario to Chicago (YHM to CHI) flight deals and tips

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

Fastest flight time

13h 26m

Direct flights

None
The fastest flight from Hamilton, Ontario to Chicago takes 13h 26m
There are no direct flights from Hamilton, Ontario to Chicago. There are no popular flight routes from Hamilton, Ontario to Chicago.
Search flight deals

  • How far is Hamilton to Chicago by plane?

    There are 654.3 km between Hamilton and Chicago. Typically, this will take 13h 26m by plane in normal conditions.

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

    Prices for flights from Hamilton Airport to Chicago refresh daily.

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

  • How old do you have to be to fly from Hamilton 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 Hamilton 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 airline from Hamilton, Ontario to Chicago?

Best airlines flying from Hamilton, Ontario to Chicago

Compare and see reviews for airlines that fly from Hamilton, Ontario to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom C$ 303Free CancellationRating
7.1
10,828 reviews
Search Air Canada flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Munster
Hammond

Why use momondo?

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

It is quick and easy to find Hamilton to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Yes. All flights to Chicago from Hamilton on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo helps you find the best flight between Hamilton and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Yes. momondo can track prices for Hamilton to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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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 25.6 km from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport