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Cheap flights from Hamilton to Chicago

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Compare Hamilton to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

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Flight deals from Hamilton to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from Hamilton to Chicago? Find the lowest prices on one-way and round-trip tickets right here.
Chicago.C$499 per passenger.Departing Sat, May 3, returning Sun, May 11.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Hamilton on Sat, May 3, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departing from Chicago O'Hare International on Sun, May 11, arriving in Hamilton.Price includes taxes and charges.From C$499, select.
Chicago.C$510 per passenger.Departing Fri, May 30, returning Tue, Jun 3.Round-trip flight with WestJet and Spirit Airlines.Outbound indirect flight with WestJet, departing from Hamilton on Fri, May 30, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departing from Chicago O'Hare International on Tue, Jun 3, arriving in Hamilton.Price includes taxes and charges.From C$510, select.
Chicago.C$592 per passenger.Departing Sat, Jun 14, returning Mon, Jun 16.Round-trip flight with Porter Airlines (Canada) Ltd and WestJet.Outbound indirect flight with Porter Airlines (Canada) Ltd, departing from Hamilton on Sat, Jun 14, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departing from Chicago O'Hare International on Mon, Jun 16, arriving in Hamilton.Price includes taxes and charges.From C$592, select.
Chicago.C$606 per passenger.Departing Sun, Aug 17, returning Wed, Aug 20.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Hamilton on Sun, Aug 17, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departing from Chicago O'Hare International on Wed, Aug 20, arriving in Hamilton.Price includes taxes and charges.From C$606, select.
Chicago.C$634 per passenger.Departing Wed, Jul 16, returning Sun, Jul 20.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Hamilton on Wed, Jul 16, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departing from Chicago O'Hare International on Sun, Jul 20, arriving in Hamilton.Price includes taxes and charges.From C$634, select.
Chicago.C$860 per passenger.Departing Sat, Sep 27, returning Tue, Sep 30.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Hamilton on Sat, Sep 27, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departing from Chicago O'Hare International on Tue, Sep 30, arriving in Hamilton.Price includes taxes and charges.From C$860, select.
Chicago.C$878 per passenger.Departing Fri, Sep 19, returning Fri, Oct 24.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Hamilton on Fri, Sep 19, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departing from Chicago O'Hare International on Fri, Oct 24, arriving in Hamilton.Price includes taxes and charges.From C$878, select.
Chicago.C$938 per passenger.Departing Mon, Aug 25, returning Mon, Sep 8.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Hamilton on Mon, Aug 25, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departing from Chicago O'Hare International on Mon, Sep 8, arriving in Hamilton.Price includes taxes and charges.From C$938, select.

Find the cheapest month to fly from Hamilton to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Hamilton to Chicago flights are currently cheapest in May.
Mar
Find prices
Apr
from C$968
May
from C$499
Jun
from C$592
Jul
from C$634
Aug
from C$606
Sep
from C$860
Oct
from C$1,025
Nov
Find prices
Dec
Find prices
Jan
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Feb
Find prices

Alternative Hamilton to Chicago routes

Looking for the cheapest, fastest or easiest route from Hamilton to Chicago? You could fly into the following airports instead.

Toronto to Chicago: Flight information

The things to know before you go.
Cheapest flight foundC$499
Cheapest month to flyMay

Finding cheap flights from Hamilton to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a round-trip flight from Hamilton to Chicago is C$499. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Hamilton to Chicago. But we found flights with one or more stops from C$499.
There are no flights flying from Hamilton to Chicago, as of March 2025.
The cheapest month to fly from Hamilton to Chicago is usually March 2025.
If you're flying from Hamilton Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the center of Chicago. We've found flights to this airport from C$499.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Hamilton Airport to Chicago on Saturday, May 3, 2025.
No airlines currently offer direct flights between Hamilton Airport and Chicago. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In March, the average temperature is usually around 3°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, WestJet offers the cheapest flight tickets to Chicago.

How to find cheap flights to Chicago from Hamilton

Looking for cheap tickets from Hamilton to Chicago? Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

  • Simply hit "search." From Delta Air Lines to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from Hamilton to Chicago. And with us, there are no hidden fees – what you see is what you pay.
  • Compare flight deals to Chicago from Hamilton from over 1,000 providers. Then choose the cheapest plane tickets or fastest journeys.
  • Flex your dates to find the best Hamilton–Chicago ticket prices. If you're flexible when it comes to your travel dates, use Skyscanner's "Whole month" tool to find the cheapest month, and even day to fly to Chicago from Hamilton.
  • Set up a Price Alert. You can easily track the fare of your cheap Hamilton–Chicago flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
  • Fly without stops. Only interested in direct flights between Hamilton and Chicago? Make sure to tick "Direct flights only" when performing a search. If there are direct flights available on the route, these will appear in the results.
  • Find the cheapest Business Class flights from Hamilton and Chicago. We scour the Internet for the best Business, Premium Economy and First Class flight fares to Chicago, too. Check the difference in price as you search – you might just stumble on a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
  • Include nearby airports in your search. Widen your search for Hamilton to Chicago flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save the next time you travel.

    • Combine your flight to Chicago from Hamilton with hotels and car rental

    Once you've secured your cheap flight ticket from Hamilton to Chicago, discover the best prices and exclusive rates for hotels in Chicago or nearby. You can also compare hundreds of car rental companies at once so you get the best car rental price for your trip.


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Prices shown on this page are estimated lowest prices only. Found in the last 45 days.