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Cheap flight tickets from Hamilton to Chicago

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Compare Hamilton to Chicago flight deals

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Flight deals from Hamilton to Chicago

Looking for a cheap last-minute deal or the best return flight from Hamilton to Chicago? Find the lowest prices on one-way and return tickets right here.
Chicago.RM3,006 per passenger.Departing Sun, 8 Jun, returning Thu, 12 Jun.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Hamilton on Sun, 8 Jun, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Thu, 12 Jun, arriving in Hamilton.Price includes taxes and charges.From RM3,006, select.
Chicago.RM3,291 per passenger.Departing Sat, 28 Jun, returning Sat, 5 Jul.Return flight with WestJet and Frontier Airlines.Outbound indirect flight with WestJet, departs from Hamilton on Sat, 28 Jun, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sat, 5 Jul, arriving in Hamilton.Price includes taxes and charges.From RM3,291, select.
Chicago.RM3,399 per passenger.Departing Thu, 4 Sep, returning Thu, 11 Sep.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Hamilton on Thu, 4 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Thu, 11 Sep, arriving in Hamilton.Price includes taxes and charges.From RM3,399, select.
Chicago.RM3,469 per passenger.Departing Sat, 23 Aug, returning Mon, 25 Aug.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Hamilton on Sat, 23 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Mon, 25 Aug, arriving in Hamilton.Price includes taxes and charges.From RM3,469, select.
Chicago.RM3,642 per passenger.Departing Fri, 30 May, returning Sun, 1 Jun.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Hamilton on Fri, 30 May, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Sun, 1 Jun, arriving in Hamilton.Price includes taxes and charges.From RM3,642, select.
Chicago.RM3,850 per passenger.Departing Thu, 28 Aug, returning Sat, 6 Sep.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Hamilton on Thu, 28 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Sat, 6 Sep, arriving in Hamilton.Price includes taxes and charges.From RM3,850, select.
Chicago.RM3,890 per passenger.Departing Sun, 16 Nov, returning Sun, 23 Nov.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Hamilton on Sun, 16 Nov, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Sun, 23 Nov, arriving in Hamilton.Price includes taxes and charges.From RM3,890, select.
Chicago.RM3,975 per passenger.Departing Fri, 11 Jul, returning Mon, 14 Jul.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Hamilton on Fri, 11 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Mon, 14 Jul, arriving in Hamilton.Price includes taxes and charges.From RM3,975, 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 June.
May
from RM4,837
Jun
from RM3,006
Jul
from RM3,975
Aug
from RM3,469
Sep
from RM3,399
Oct
from RM4,233
Nov
from RM3,890
Dec
Find prices
Jan
Find prices
Feb
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Mar
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Apr
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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 foundRM3,006
Cheapest month to flyJune

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 return flight from Hamilton to Chicago is RM3,006. 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 RM3,006.
As of May 2025, there are no flights flying from Hamilton to Chicago.
The cheapest month to fly from Hamilton to Chicago is usually May 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 centre of Chicago. We've found flights into this airport from RM3,006.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Hamilton Airport to Chicago on Sunday, 8 June 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 May, the average temperature is usually around 13°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.

Travelling from John C. Munro Hamilton Airport (YHM) to Chicago: what you need to know

  • John C. Munro Hamilton Airport is located in Toronto. Based in the UTC-5 timezone, Chicago is one hour behind Toronto.

  • For a smooth journey, arrive at the airport two hours ahead of international flights and one hour before domestic departures. This will give you enough time to catch your YHM to Chicago flight.

  • If you're flying during a major holiday or another peak period, allow extra time. A good general rule is two hours ahead of domestic flights and up to four hours before international departures. Check-in and security lines will be longer.

  • The journey from central Toronto to YHM takes around 3 hours 20 minutes on public transport. If you drive, ride-share or grab a cab, you'll cover the 72 kilometres in 1 hour or so, depending on traffic conditions.

  • Planning to catch an early flight from John C. Munro Hamilton Airport to Chicago? Avoid rushing to the airport (and enjoy a little extra shut-eye) by choosing one of these hotels near YHM:

  • When it comes to the on-time performance of John C. Munro Hamilton Airport, data shows 71.43% of flights stick to their scheduled arrival time.

How to find the cheapest flights from John C. Munro Hamilton Airport (YHM) to Chicago

  • RM1,560 is the cheapest price we've seen for a one-way John C. Munro Hamilton Airport to Chicago flight. A return flight ticket right now is RM3,006. Depending on how early you book and the availability, these fares could change.

  • To pick up cheap flights from YHM to Chicago, book as early as possible. Airlines generally offer their most competitively priced fares when flights are first released.

  • Finding cheap tickets from John C. Munro Hamilton Airport to Chicago is easier if you're flexible with your dates. Try using the 'Whole month' tool to access the best prices across every month and snap up an incredible deal.

  • Finding a cheap flight from YHM to Chicago couldn't be easier with Price Alerts. All you need to do is set up one of these automatic notifications and we'll let you know when there's a better deal.

  • Pick your ideal departure and arrival times, number of stops and airlines with our filters. Then, sort the results for your flight from John C. Munro Hamilton Airport to Chicago by 'Cheapest,' 'Fastest' or 'Best.'

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) to the centre of Chicago takes about 35 minutes to reach by car. The centre is roughly 40 kilometres away.

  • It takes around 55 minutes to get there by public transport.

  • Book a hotel close to ORD if you're coming in on a late flight from John C. Munro Hamilton Airport to Chicago. Select one of these options and make your arrival easier:

  • Pick up an O'Hare International Airport rental car and discover Chicago and beyond with your own wheels. Routes Car Rentals, Dollar and Budget are top outlets to choose from here.

  • For the lowest price, book your vehicle from O'Hare International Airport about four weeks in advance of your flight from YHM to Chicago.

  • The street address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Central Chicago is located around 19 kilometres from Chicago Midway International Airport (MDW). After your flight from John C. Munro Hamilton Airport to Chicago has landed and you've navigated your way to arrivals, the drive should take about 20 minutes.

  • The journey will take about 45 minutes on public transport.

  • You'll find some comfortable places to drop your things at near MDW. Kick back and get cosy after your YHM to Chicago flight at any of these perfectly located options:

  • The fastest way to get to where you're going is with a Chicago Midway International Airport rental car. Grab your wheels from Dollar, Hertz or Budget and make a speedy getaway.

  • Call dibs on the best options. Booking your ride from MDW four weeks ahead of time often means lower prices and a wider choice of vehicles.

  • You can find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Hop off your flight from John C. Munro Hamilton Airport to Chicago and make your way to your hotel or jump right into exploring. The centre of Chicago is around 137 kilometres from Chicago Rockford International Airport (RFD) and typically takes 1 hour 25 minutes to drive there.

  • Public transport will get you there in about 4 hours 15 minutes.

  • If you don't want to make the trip to the centre, choose a hotel close to RFD. Settle in at one of these stays after your YHM to Chicago flight:

  • Begin your travels without stressing about how to get to your destination with a Chicago Rockford International Airport rental car. You can book with trusted companies here like Budget, Alamo and National.

  • If you'd like a certain model or make, booking early increases your chances of getting your first choice. Secure your ride from RFD at least a few weeks ahead of your flight from John C. Munro Hamilton Airport to Chicago.

  • The street address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

  • Carefully consider your travel dates before booking your flight from John C. Munro Hamilton Airport to Chicago. The city comes alive in peak season, but hotel prices are generally higher and top attractions can get crowded. Plan your trip to Chicago in low season if you want a quieter vibe.

  • Before locking in your John C. Munro Hamilton Airport to Chicago flight ticket, think about what kind of weather works for you. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • January sees average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Search for a cheap ticket from YHM to Chicago around that time if you like cooler conditions.

More about Chicago

Explore more of United States

  • Chicago has its own special appeal, but there are so many other parts of United States waiting to be explored. Around 451 kilometres south-east of Chicago, a visit to Columbus will keep your itinerary busy. Don't miss top attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another favourite stop in United States. Start your sightseeing at The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Plan the rest of your trip from Toronto to Chicago

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