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Cheap flights from Hamilton, Ontario to Chicago from $173

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 7/30. 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
0 bags

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
8:15 am - 11:15 pm
YHM
-
ORD
16h 00m
1 stop
Multiple Airlines Logo
5:05 am - 3:55 pm
ORD
-
YHM
9h 50m
1 stop
$441Multiple Airlines
Sat, May 23 - Mon, May 25
Multiple Airlines Logo
8:15 am - 11:15 pm
YHM
-
ORD
16h 00m
1 stop
Multiple Airlines Logo
5:05 am - 3:55 pm
ORD
-
YHM
9h 50m
1 stop
$472Multiple Airlines
Sat, May 30 - Sat, Jun 6
Multiple Airlines Logo
8:15 am - 9:54 am
YHM
-
ORD
26h 39m
2 stops
Multiple Airlines Logo
5:05 am - 3:55 pm
ORD
-
YHM
9h 50m
1 stop
$484Multiple Airlines
Sat, May 23 - Mon, May 25
Multiple Airlines Logo
8:15 am - 7:29 pm
YHM
-
ORD
36h 14m
2 stops
Multiple Airlines Logo
5:30 pm - 11:13 pm
ORD
-
YHM
28h 43m
1 stop
$557Multiple Airlines
Mon, Jun 1 - Sat, Jun 6
Multiple Airlines Logo
8:15 am - 11:15 pm
YHM
-
ORD
16h 00m
1 stop
Multiple Airlines Logo
5:05 am - 3:55 pm
ORD
-
YHM
9h 50m
1 stop
$563Multiple Airlines
Mon, Jun 1 - Sat, Jun 6
Multiple Airlines Logo
6:10 pm - 4:40 pm
YHM
-
ORD
23h 30m
1 stop
Multiple Airlines Logo
5:30 pm - 10:14 pm
ORD
-
YHM
27h 44m
2 stops
$587Multiple Airlines
Fri, May 22 - Sun, May 24
Multiple Airlines Logo
8:15 am - 7:29 pm
YHM
-
ORD
36h 14m
2 stops
Multiple Airlines Logo
5:30 pm - 5:15 pm
ORD
-
YHM
22h 45m
1 stop
$590Multiple Airlines
Mon, Jun 1 - Sat, Jun 6
Multiple Airlines Logo
8:15 am - 7:29 pm
YHM
-
ORD
36h 14m
2 stops
Multiple Airlines Logo
5:30 pm - 11:13 pm
ORD
-
YHM
28h 43m
1 stop
$591Multiple Airlines
Mon, Jun 1 - Mon, Jun 8
Multiple Airlines Logo
5:45 pm - 4:40 pm
YHM
-
ORD
23h 55m
2 stops
Multiple Airlines Logo
5:30 pm - 10:34 pm
ORD
-
YHM
28h 04m
2 stops
$592Multiple Airlines
Thu, May 28 - Sun, May 31
Multiple Airlines Logo
8:15 am - 9:54 am
YHM
-
ORD
26h 39m
2 stops
Multiple Airlines Logo
5:05 am - 3:55 pm
ORD
-
YHM
9h 50m
1 stop
$610Multiple Airlines
Sat, May 30 - Sat, Jun 6

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WestJet flights from Hamilton, Ontario to Chicago

Our best WestJet deals on Hamilton, Ontario to Chicago flight tickets
WestJet
May 21
YHM6:10 pmHamilton
23h 30m
1 stop
ORD4:40 pmChicago O'Hare Intl
May 24
ORD5:30 pmChicago O'Hare Intl
22h 45m
1 stop
YHM5:15 pmHamilton
$892
WestJet
May 18
YHM6:10 pmHamilton
23h 30m
1 stop
ORD4:40 pmChicago O'Hare Intl
May 20
ORD5:30 pmChicago O'Hare Intl
22h 45m
1 stop
YHM5:15 pmHamilton
$1,118
WestJet
May 7
YHM6:10 pmHamilton
23h 30m
1 stop
ORD4:40 pmChicago O'Hare Intl
May 25
ORD5:30 pmChicago O'Hare Intl
22h 45m
1 stop
YHM5:15 pmHamilton
$1,359

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 832,500 searches. Data last updated May 6, 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
Quickest round-trip

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sat 5/23

8:15 am-11:15 pm

1 stop16h 00m

Chicago O'Hare Intl

Mon 5/25

5:05 am-3:55 pm

1 stop9h 50m

$441

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sat 5/30

8:15 am-11:15 pm

1 stop16h 00m

Chicago O'Hare Intl

Sat 6/6

5:05 am-3:55 pm

1 stop9h 50m

$472

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sat 5/23

8:15 am-9:54 am

2 stops26h 39m

Chicago O'Hare Intl

Mon 5/25

5:05 am-3:55 pm

1 stop9h 50m

$484

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Mon 6/1

8:15 am-7:29 pm

2 stops36h 14m

Chicago O'Hare Intl

Sat 6/6

5:30 pm-11:13 pm

1 stop28h 43m

$557

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Mon 6/1

8:15 am-11:15 pm

1 stop16h 00m

Chicago O'Hare Intl

Sat 6/6

5:05 am-3:55 pm

1 stop9h 50m

$563

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Fri 5/22

6:10 pm-4:40 pm

1 stop23h 30m

Chicago O'Hare Intl

Sun 5/24

5:30 pm-10:14 pm

2 stops27h 44m

$587

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Mon 6/1

8:15 am-7:29 pm

2 stops36h 14m

Chicago O'Hare Intl

Sat 6/6

5:30 pm-5:15 pm

1 stop22h 45m

$590

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Mon 6/1

8:15 am-7:29 pm

2 stops36h 14m

Chicago O'Hare Intl

Mon 6/8

5:30 pm-11:13 pm

1 stop28h 43m

$591

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Thu 5/28

5:45 pm-4:40 pm

2 stops23h 55m

Chicago O'Hare Intl

Sun 5/31

5:30 pm-10:34 pm

2 stops28h 04m

$592

HamiltonChicago

YHM - ORD

YHMORD

Hamilton

Sat 5/30

8:15 am-9:54 am

2 stops26h 39m

Chicago O'Hare Intl

Sat 6/6

5:05 am-3:55 pm

1 stop9h 50m

$610

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 typical price of a round-trip flight between Hamilton, Ontario and Chicago?

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Hamilton, Ontario, with most prices found around $0. If you’re not able to fly to Chicago in February, then January is your next best option. Flight prices from Hamilton, Ontario to Chicago during January average around $0.

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 $437. 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 Hamilton, Ontario to Chicago for around $690.

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 Hamilton, Ontario to Chicago during this time can be as low as $405. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $665.

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

10h 53m

Direct flights

None
The fastest flight from Hamilton, Ontario to Chicago takes 10h 53m
There are no direct flights from Hamilton, Ontario to Chicago. There are no popular flight routes from Hamilton, Ontario to Chicago.
Search flight deals

Frequently asked questions about flying from Hamilton, Ontario to Chicago

  • How far is Hamilton to Chicago by plane?

    Chicago is 406.6 mi away from Hamilton. A reasonable flight in good conditions will take 10h 53m.

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

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

  • 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 required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Traveling to a place near Chicago?

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

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Hamilton to Chicago for you.

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

Flights from Hamilton to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search for Hamilton to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Of course. momondo tracks the price of Hamilton to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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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