'How To Get The Best Deal' Guides

Monday, June 17th 2024

"I'm a travel junkie who's hooked on deals from YYC." - Chris Myden

2024
22
May
Calgary to Chicago, Illinois - $258 CAD roundtrip including taxes [Nonstop Flights]

Chicago

WestJet has dropped the price of a few of their May and June 2024 flights from Calgary to Chicago, Illinois down to $263 CAD roundtrip including taxes.

The flights are nonstop both ways.

UPDATE - A few dates in June are available for $258 CAD roundtrip, including a Friday to Sunday flight.



Availability for travel

May, June, July, August 2024

How to find and book this deal

1. Start with the following Google Flights search:

Google Flights: Calgary to Chicago

- Click on the departure date box to open up the calendar view and browse for cheap date combinations.

- Adjust the trip length at the bottom.

- Look for the dates that are $274 to $314 roundtrip

2. Go to Kayak or Skyscanner

3. Search for a flight from Calgary (YYC) to Chicago (ORD)

- Try the same dates you found on Google Flights.

[Cheapest Dates]

May 16 to May 18
May 19 to May 26, 30
May 23 to May 26 -- weekend
May 24 to May 30, Jun 1

May 25 to May 30, Jun 1
May 31 to Jun 6

Jun 1 to Jun 8

Hotel Deals in Chicago

Places to stay in Chicago with great reviews start at around $125 CAD per night.

Try this search on Kayak for properties with a score of 8 out of 10 or higher.

You can sort by price near the top of the results.

Can't find this deal anymore? Prices change as deals sell out. The key is to be among the first to know when an amazing deal is posted.

Click here for tips on how to never miss a deal again.





screenshot from Kayak



Sign up for YYC Deals Alerts from Calgary

Go to the Alerts Page to sign up for flight deal alerts by e-mail, Facebook, or Twitter.

Travellers from Calgary also often sign up for alerts from Edmonton and Vancouver.

Join us in the YYC Deals Facebook Group

For live discussion of this deal, or to get some amazing travel advice (about anywhere) from your 50,000 fellow passengers in Calgary, join us in the:
YYC Deals Facebook Group.
^^^ click the 'Join Group' button when you arrive.

Hit Like if you like this deal! Click Share to show your friends on Facebook.



2024
20
May
Calgary to Hawaii for under $395 CAD roundtrip including taxes

Hawaii

Read more



2024
16
May
Calgary to Halifax, Nova Scotia (or vice versa) - $290 CAD roundtrip including taxes [Nonstop Flights]

Halifax, Nova Scotia

Read more



2024
15
May
Calgary to St. John's or Deer Lake, Newfoundland - $287 to $357 CAD roundtrip including taxes | Nonstop Flights

Newfoundland

Read more



2024
15
May
Calgary to Tokyo, Japan - $922 CAD roundtrip including taxes [Nonstop Flights, Off Season]

Tokyo, Japan

Read more



2024
15
May
Calgary to Charlottetown, PEI - $318 CAD roundtrip including taxes | Nonstop Flights

Charlottetown, PEI

Read more



2024
13
May
Calgary to Deer Lake, Newfoundland - $222 CAD roundtrip including taxes [Nonstop Flights, New Record!]

Gros Morne, Newfoundland

Read more



2024
11
May
Calgary to Montreal - $286 CAD roundtrip including taxes [Nonstop Flights]

Montreal, Quebec

Read more



2024
11
May
Calgary to Yellowknife, Northwest Territories (or vice-versa) - $216 CAD roundtrip including taxes [Nonstop Flights]

Yellowknife, Northwest Territories

Read more



2024
11
May
Calgary to Nashville, Tennessee - $263 CAD roundtrip including taxes [Nonstop Flights]

Nashville, Tenneseee

Read more



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(click 'Join Group' when you arrive)