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This Weekend's Flight Deals from Vancouver to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Airfares from $177 One Way, $312 Round Trip from Vancouver to Chicago

Prices starting at $312 for return flights and $177 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Need A Hotel In Chicago After Your Flight?

Hotels In Top Chicago Neighborhoods

Near North Side
241 hotels

ACME Hotel Company

3.5 out of 5.0


The Loop
142 hotels


108 hotels

City Suites Hotel

3.0 out of 5.0


Stay Near Exciting Chicago Attractions

More About Flying To Chicago from Vancouver

Route Information for Flights from Vancouver to Chicago

Origin Airport IATA CodeYVR
Destination Airport IATA CodeCHI
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Flights Review

Sep 18, 2019

bathroom was so small that I could not get close enough to the urinal to pee because I am 6ft 4 madey for somebody that fiver nine

Aug 21, 2019

One of the staff on board was very helpful with my bag when I couldn’t get it to fit under the seat & he put it up above for me. Though I was disappointed with the tiny space under the seat that the bag I usually travel with would not fit. I have a cpap & instead of carrying a separate bag for it I that can get forgotten, I consolidate it with my book, purse items, snacks, pillow, & sweater in one larger tote with wheels.

Jun 25, 2019

Boarding process should be back of plane first

Jun 3, 2019

Since we can’t have phones on plane, we were unaware our flight changed. We stopped when exiting the plane to ask our gate since it wasn’t on ticket. Wish the gate staff could have told us it was delayed. We rushed to our gate and were in line for a wrong flight when we noticed it said LAS Vegas.

Sep 29, 2018

Seats were the smallest I’ve ridden on.

Sep 18, 2018

The only problem we had was arriving into Louisville, KY, it took the staff a very long time to get the ramp attached to the door so that we could leave the plane. We touched down at 12:10 am and did not vacate the plane until 12:50 am.

Sep 5, 2018

The attendants and pilots were great! They allowed my 6 year old to take a peek at the cocklpit. She was thrilled!

Jul 5, 2018

Great flight and very friendly staff. Comfortable seats and very roomy.

Jul 2, 2018

both flights departed and arrived even a little early.

Jun 24, 2018

We were grateful for the safe and smooth flights! Big thanks to the pilots!

Travel from Vancouver to Chicago can help locate discount vacation packages, hotel accommodations and other ways to save on your trip from Vancouver to Chicago. Vancouver is one of the largest cities in Canada, and it is one of the nation's largest industrial centers. Chicago is the largest city in Illinois and has close to 50 million visitors each year.


The Vancouver International Airport is located 7 miles from downtown Vancouver. It is the second-busiest airport in Canada. There are several methods of transportation to the airport from downtown. The Canada Line is a rapid rail line, which is the fastest way to get to the city's center. Taxis, rental cars, buses and courtesy shuttles are also available. For those who arrive in private vehicles, economy and long-term parking lots are available at the airport. Fees can be paid by credit card at the express pay machines located at both parking facilities.


Chicago is located in the northeastern corner of the state of Illinois. The city is an international hub for finance, commerce, industry, telecommunications and transportation. Travelers arriving in Chicago from Vancouver will arrive at the Chicago O'Hare International Airport. It is located approximately 17 miles northwest of the Chicago Loop. The airport offers both domestic and international flights. Regional buses and trains, rental cars, taxicabs and limos provide transportation from the airport to downtown. The best time to visit Chicago is in the fall, when temperatures are still warm and crowds are smaller. The hottest month of the year is July, with average daytime highs around 85 degrees Fahrenheit. January is the coldest month, with overnight lows around 18 degrees Fahrenheit. Chicago offers visitors a wide variety of things to do and see. The waterfront, in particular, provides a lively nightlife. Other spots of interest include Grant Park, as well as the Lincoln Park Zoo and the Goodman Theater.

Flying to Chicago

When planning a trip, check for the best deals on discount hotel accommodations, rental cars, vacation packages and cheap flights from Vancouver to Chicago. Planning ahead of time and making travel arrangements early will allow you to save money on attractions and events.

Flights from Vancouver to Chicago - Frequently Asked Questions

If I am not able to travel due to COVID-19, can I cancel my flight to Chicago?

We get that traveling right now has its challenges, so it's good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you'll quickly see what options are available. Our Customer Service Portal is the place to go for more information.

Are there flights to Chicago with flexible change policies?

In most cases you'll have the option to reschedule your flight to Chicago without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the "no change fees" filter and book with confidence.

What is the cheapest day of the week to fly?

Consider flying out early in the week to save on your airfare. Orbitz data from 2020 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.

What is the cheapest month to fly?

We won't keep you guessing, according to Orbitz data the cheapest month to fly is August. Perfect for those who need a weekend getaway, or just a break from it all before the weather changes. Be aware that the most expensive time to fly is the height of summer, with ticket prices peaking in the month of June.

How can I save money on flights?

To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2020 saved up to 45% on their airfares. Get mixing and matching today!

*According to flight demand on from January to December 2020. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.