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Flight Deals from Vancouver to Chicago from $140

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Stops

  • Nonstop
    from $321
  • Up to 1 stop
    $209
  • Up to 2 stops
    $305

Airlines

  • Air Canada
    $305
  • Alaska Airlines
    $307
  • Delta Air Lines
    $340
  • Hahn Air
    $677
  • JetBlue
    $463
  • United Airlines
    $454
  • WestJet
    $209

Cabin Class

  • Economy
    $209

Departure Airports

  • Abbotsford Airport
    $377
  • Vancouver International Airport
    $209

Arrival Airports

  • Chicago Midway Airport
    $497
  • Chicago O Hare Airport
    $209

Layover Airports

  • Calgary International Airport
    $209
  • Denver International Airport
    $526
  • Detroit Metropolitan Airport
    $356
  • Edmonton Airport
    $305
  • Hartsfield Jackson Atlanta International Airport
    $499
  • Los Angeles International Airport
    $454
  • Minneapolis-St Paul International/Wold-Chamberlain Airport
    $497
  • Montreal Trudeau Airport
    $348
  • New York John F Kennedy Airport
    $463
  • Portland International Airport
    $323
  • Salt Lake City International Airport
    $510
  • San Francisco International Airport
    $516
  • Seattle Tacoma International Airport
    $307
  • Toronto Pearson Airport
    $305
  • Winnipeg / James Armstrong Richardson International Airport
    $338

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On average save $240 per traveler
WestJet Logo
WestJet

06/11/25

YVR
10h 44m
YYC

06/11/25

ORD
WestJet Logo
WestJet

06/17/25

ORD
5h 5m
YYC

06/17/25

YVR
$209
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/22/25

YVR
25h 14m
YYC

05/23/25

ORD
WestJet Logo
WestJet

05/29/25

ORD
6h 31m
YYC

05/30/25

YVR
$235
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/13/25

YVR
14h 10m
YEG
YYZ

06/14/25

ORD
Air Canada Logo
Air Canada

06/18/25

ORD
2h 33m
Direct

06/18/25

YVR
$305
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/14/25

YVR
14h 10m
YEG
YYZ

06/15/25

ORD
Air Canada Logo
Air Canada

06/17/25

ORD
2h 34m
Direct

06/17/25

YVR
$305
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

05/20/25

YVR
8h 29m
SEA

05/20/25

ORD
Alaska Airlines Logo
Alaska Airlines

06/11/25

ORD
6h 48m
SEA

06/11/25

YVR
$307
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/21/25

YVR
6h 13m
Direct

05/21/25

ORD
Air Canada Logo
Air Canada

06/18/25

ORD
2h 33m
Direct

06/18/25

YVR
$321
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/23/25

YVR
6h 13m
Direct

05/23/25

ORD
Air Canada Logo
Air Canada

06/18/25

ORD
2h 33m
Direct

06/18/25

YVR
$321
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

06/04/25

YVR
10h 11m
SEA

06/04/25

ORD
Alaska Airlines Logo
Alaska Airlines

06/11/25

ORD
6h 48m
SEA

06/11/25

YVR
$322
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

06/05/25

YVR
10h 39m
PDX

06/05/25

ORD
Alaska Airlines Logo
Alaska Airlines

06/11/25

ORD
6h 48m
SEA

06/11/25

YVR
$323
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

06/06/25

YVR
10h 39m
PDX

06/06/25

ORD
Alaska Airlines Logo
Alaska Airlines

06/11/25

ORD
6h 48m
SEA

06/11/25

YVR
$332
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/17/25

YVR
6h 13m
Direct

05/17/25

ORD
Air Canada Logo
Air Canada

06/11/25

ORD
9h 4m
YYZ
YWG

06/11/25

YVR
$338
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/22/25

YVR
9h 44m
YYC

05/22/25

ORD
Delta Air Lines Logo
Delta Air Lines

05/25/25

ORD
6h 40m
YYC

05/26/25

YVR
$340
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

05/17/25

YVR
14h 27m
YYC
YUL

05/18/25

ORD
Air Canada Logo
Air Canada

06/11/25

ORD
9h 4m
YYZ
YWG

06/11/25

YVR
$348
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/22/25

YVR
13h 37m
YYC
DTW

05/22/25

ORD
Delta Air Lines Logo
Delta Air Lines

05/25/25

ORD
6h 40m
YYC

05/26/25

YVR
$356
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/20/25

YXX
19h 49m
YYC

05/21/25

ORD
WestJet Logo
WestJet

06/11/25

ORD
6h 48m
SEA

06/11/25

YXX
$377
Free cancellation within 83 hours of booking
Air Canada Logo
Air Canada

06/14/25

YVR
12h 50m
YUL

06/14/25

ORD
Air Canada Logo
Air Canada

06/17/25

ORD
2h 34m
Direct

06/17/25

YVR
$417
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/22/25

YVR
6h 16m
Direct

05/22/25

ORD
United Airlines Logo
United Airlines

05/24/25

ORD
7h 43m
LAX

05/24/25

YVR
$454
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

05/27/25

YVR
16h 39m
JFK

05/28/25

ORD
JetBlue Logo
JetBlue

06/04/25

ORD
14h 50m
JFK

06/04/25

YVR
$463
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/22/25

YVR
12h 34m
LAX

05/22/25

ORD
United Airlines Logo
United Airlines

05/24/25

ORD
7h 43m
LAX

05/24/25

YVR
$470
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

06/06/25

YXX
12h 5m
YYC
MSP

06/06/25

MDW
WestJet Logo
WestJet

06/17/25

MDW
6h 40m
YYC

06/18/25

YXX
$497
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

06/11/25

YXX
11h 6m
YYC
MSP

06/11/25

ORD
WestJet Logo
WestJet

06/17/25

ORD
6h 40m
YYC

06/18/25

YXX
$497
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

06/12/25

YXX
12h 23m
YYC
DTW

06/12/25

ORD
WestJet Logo
WestJet

06/16/25

ORD
6h 40m
YYC

06/17/25

YXX
$497
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

06/14/25

YVR
15h 39m
YYC
ATL

06/15/25

ORD
WestJet Logo
WestJet

06/15/25

ORD
6h 40m
YYC

06/16/25

YVR
$499
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/20/25

YVR
10h 44m
YYC

05/20/25

ORD
WestJet Logo
WestJet

06/12/25

ORD
8h 30m
SLC
YEG

06/12/25

YVR
$510
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/23/25

YVR
10h 44m
YYC

05/23/25

ORD
WestJet Logo
WestJet

06/05/25

ORD
8h 40m
SLC
YEG

06/05/25

YVR
$510
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/02/25

YVR
12h 19m
SFO

06/03/25

ORD
United Airlines Logo
United Airlines

06/05/25

ORD
2h 43m
Direct

06/05/25

YVR
$516
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/02/25

YVR
11h 59m
LAX

06/02/25

ORD
United Airlines Logo
United Airlines

06/05/25

ORD
15h 19m
DEN

06/06/25

YVR
$526
Free cancellation within 83 hours of booking
WestJet Logo
WestJet

05/31/25

YXX
15h 33m
YYC
ATL

05/31/25

MDW
WestJet Logo
WestJet

06/02/25

MDW
5h 5m
YYC

06/02/25

YXX
$529
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/22/25

YVR
11h 4m
LAX

05/22/25

ORD
United Airlines Logo
United Airlines

05/24/25

ORD
8h 6m
DEN
SFO

05/24/25

YVR
$654
Free cancellation within 83 hours of booking
Hahn Air Logo
Hahn Air

05/25/25

YVR
18h 1m
PDX

05/26/25

ORD
Hahn Air Logo
Hahn Air

06/02/25

ORD
10h 17m
SEA
PDX

06/02/25

YVR
$677
Free cancellation within 83 hours of booking

Top Deals on flights from Vancouver to Chicago

Vancouver, CA (YVR) - Chicago, US (CHI)

WestJet Logo
WestJet

May 20

YVR
10h 44m
YYC

May 20

ORD

as low as

$140

Vancouver, CA (YVR) - Chicago, US (CHI)

WestJet Logo
WestJet

May 31

YXX
25h 54m
YYC

Jun 1

ORD

as low as

$147

Vancouver, CA (YVR) - Chicago, US (CHI)

Alaska Airlines Logo
Alaska Airlines

Jun 4

YVR
10h 11m
SEA

Jun 4

ORD

as low as

$178

Vancouver, CA (YVR) - Chicago, US (CHI)

Alaska Airlines Logo
Alaska Airlines

Jun 5

YVR
10h 39m
PDX

Jun 5

ORD

as low as

$178

Vancouver, CA (YVR) - Chicago, US (CHI)

Air Canada Logo
Air Canada

Jun 4

YVR
6h 13m
Direct

Jun 4

ORD

as low as

$180

Vancouver, CA (YVR) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jun 11

YVR
6h 6m
Direct

Jun 12

ORD

as low as

$180

Vancouver, CA (YVR) - Chicago, US (CHI)

United Airlines Logo
United Airlines

May 20

YVR
6h 16m
Direct

May 21

ORD

as low as

$180

Vancouver, CA (YVR) - Chicago, US (CHI)

Alaska Airlines Logo
Alaska Airlines

May 31

YVR
10h 42m
PDX
SEA

May 31

ORD

as low as

$188

Vancouver, CA (YVR) - Chicago, US (CHI)

Air Canada Logo
Air Canada

May 27

YVR
14h 27m
YYC
YUL

May 28

ORD

as low as

$190

Vancouver, CA (YVR) - Chicago, US (CHI)

Air Canada Logo
Air Canada

Jun 3

YVR
11h 24m
YYZ

Jun 4

ORD

as low as

$191

Vancouver, CA (YVR) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 19

YVR
11h 12m
DFW

May 19

ORD

as low as

$195

Vancouver, CA (YVR) - Chicago, US (CHI)

United Airlines Logo
United Airlines

May 25

YVR
12h 34m
LAX

May 25

ORD

as low as

$195

Frequently Asked Questions

What is the typical flight duration from Vancouver to Chicago?
The typical flight duration from Vancouver to Chicago usually ranges between 4 to 5 hours, depending on weather and air traffic conditions. This direct flight time can vary slightly with seasonal scheduling and chosen airline routes. Travelers can expect a comfortable journey provided they check in early and stay updated on potential delays. Knowing this timeframe helps in planning connecting ground transportation and subsequent activities in Chicago.
Are there any direct flights from Vancouver to Chicago?
Yes, there are direct flights available from Vancouver to Chicago. These non-stop options generally take around 4 to 5 hours, which saves time compared to connecting flights. Direct flights simplify the travel process by reducing potential delays from layovers, making your journey smoother. It’s advisable to check schedules in advance, as prices and availability can vary seasonally. Booking early often yields competitive fares, and this streamlined option is popular among travelers making the trip between Vancouver and Chicago.
What are the best transportation options from Chicago airport to downtown?
For travelers arriving in Chicago from Vancouver, the best transportation options include rideshare services, taxis, and public transit. From major airports like O’Hare, you can use the CTA Blue Line with fares typically ranging from $5 to $10, which provides a convenient and budget-friendly option. Alternatively, taxis and rideshares may cost between $30 to $50 and take around 30 to 45 minutes to downtown, depending on traffic. Consider airport shuttles as well for group travel, ensuring a smooth transition into downtown Chicago.
What are the must-see attractions in Chicago for travelers arriving from Vancouver?
Travelers from Vancouver to Chicago should not miss iconic attractions such as Millennium Park with its impressive Cloud Gate sculpture, the Navy Pier offering waterfront activities, and the Art Institute of Chicago renowned for its extensive art collections. Additionally, exploring the Magnificent Mile for its vibrant shopping and dining scene, and taking an architecture river cruise are highly recommended. Each landmark offers a distinctive slice of Chicago’s cultural and historic identity, ensuring a memorable visit filled with enriching experiences.
Which local dishes should travelers from Vancouver try when visiting Chicago?
When visiting Chicago, travelers from Vancouver should indulge in the city’s signature culinary delights. Notable local dishes include the famous deep-dish pizza with its rich tomato sauce and loaded toppings, a classic Chicago-style hot dog featuring unique toppings and a poppy seed bun, as well as Italian beef sandwiches known for their tender, thinly sliced meat. Sampling delicacies at local eateries will provide an authentic taste of Chicago’s vibrant food scene, often offered in a variety of price ranges and portion sizes to suit different appetites.
What are the best family-friendly activities in Chicago for visitors from Vancouver?
Family-friendly activities in Chicago are plentiful and cater to varied interests. Visitors from Vancouver can explore the interactive exhibits at the Museum of Science and Industry, immerse themselves in aquatic wonders at the Shedd Aquarium, or enjoy wildlife at Lincoln Park Zoo, which is free of charge. Additionally, spending time at Navy Pier with its rides, Ferris wheel, and kid-friendly attractions makes for a fun day out. These activities offer engaging experiences with costs typically ranging from free entry to modest admission fees of $20 to $40 per attraction.
Are there any budget-friendly hotels in Chicago for travelers from Vancouver?
Yes, Chicago offers several budget-friendly accommodations that cater to travelers from Vancouver. Many hotels and motels in neighborhoods near the downtown area fall within a price range of approximately $80 to $150 per night. These options provide essential amenities such as free Wi-Fi, continental breakfasts, and convenient access to public transport. Researching online and booking in advance can often secure competitive rates. Additionally, consider centrally located hostels or alternative lodging options that focus on providing quality services without excessive cost.
What are the top cultural experiences in Chicago for travelers arriving from Vancouver?
Chicago’s cultural experiences are rich and diverse, offering travelers from Vancouver an immersive journey into the city’s artistic and historical landscape. Visiting the Art Institute of Chicago and the Field Museum provides insights into fine art and natural history, while attending a performance at the Chicago Theatre or the Lyric Opera offers live entertainment. Exploring neighborhoods like Pilsen and Chinatown reveals unique cultural festivals, murals, and local cuisines. Each experience is designed to highlight Chicago’s multicultural heritage, with options available at various price ranges and venue styles.
What are the customs requirements for travelers flying from Vancouver to Chicago?
Travelers flying from Vancouver to Chicago must comply with United States customs regulations. This means ensuring you have a valid passport and, if required, an appropriate visa or ESTA approval. It is essential to declare any items that surpass duty-free limits or are subject to restrictions. Customs forms are usually provided during your flight or upon arrival, with processing times varying from 15 to 30 minutes. Preparing all necessary documentation beforehand ensures a smooth passage through customs and minimizes stress when entering the United States.
Is there a specific time of year when Chicago is best visited by travelers from Vancouver?
Yes, many travelers from Vancouver find that Chicago is best visited during late spring to early fall. The period from May to September typically offers pleasant weather with mild temperatures and clear skies, ideal for exploring outdoor attractions and festivals. Summer months also provide a lively atmosphere with a range of events and food festivals. Alternatively, early fall presents colorful foliage and fewer crowds. Whichever season you choose, be sure to monitor weather forecasts and book accommodations ahead to secure the best rates.
What are the best shopping areas in Chicago for travelers from Vancouver?
Chicago boasts vibrant shopping districts that appeal to a diverse range of tastes. Travelers from Vancouver should explore The Magnificent Mile for high-end boutiques, department stores, and luxury brands, while State Street offers a mix of chain retailers and unique shops. Neighborhood areas, such as Wicker Park and Lincoln Park, provide local designer stores and quaint indie boutiques. Whether seeking upscale fashion or unique souvenirs, these shopping areas offer a variety of price ranges, often from affordable local items to designer products. Plan visits during weekdays to avoid larger crowds.
Are there any seasonal events in Chicago that travelers from Vancouver should not miss?
Yes, Chicago hosts several seasonal events that are highlights for travelers from Vancouver. In the summer, events like the Taste of Chicago and Lollapalooza Festival showcase the city’s music, culinary, and cultural scenes. During the winter, the Christkindlmarket and holiday light displays transform the city into a festive wonderland. Spring and fall offer art festivals and outdoor street markets. Each event provides a unique cultural experience with admission costs that can range from free entry to $30 or more, making them worthwhile additions to your travel itinerary.
What safety tips should travelers from Vancouver keep in mind when visiting Chicago?
Travelers from Vancouver visiting Chicago should remain vigilant by following common safety practices. It is advisable to keep personal belongings secure and avoid carrying large amounts of cash. Use reputable transportation services, especially at night, and remain in well-populated areas. Stay informed about neighborhood safety, particularly in unfamiliar parts of the city. Additionally, consider using a money belt and secure phone storage when in crowded areas. Taking these precautions, along with regularly checking local news for safety advisories, can help ensure a smoother, more secure travel experience.
What unique airport amenities are available in Chicago for travelers arriving from Vancouver?
Chicago’s major airports, such as O’Hare, offer a range of unique amenities designed to enhance your travel experience. These include art installations and rotating exhibits that showcase local creativity, a variety of dining options with dishes reflecting the city’s diverse culinary scene, and comfortable lounges where travelers can relax before their next leg of the journey. Additionally, some terminals have interactive digital kiosks, free Wi-Fi, and spa services that range from $20 to $50. These features ensure that arriving passengers from Vancouver can unwind and experience a taste of Chicago’s hospitality right from the airport.
What are the best solo travel activities in Chicago for travelers from Vancouver?
Solo travelers from Vancouver can enjoy a variety of engaging activities in Chicago that cater to individual exploration. Consider joining a guided walking tour that explores historic districts and famous architecture, or renting a bike to cruise along the scenic lakefront paths. Museums such as the Art Institute and Field Museum offer self-guided tours, allowing visitors to set their own pace. Additionally, exploring diverse neighborhoods like Hyde Park or Lincoln Park provides opportunities to enjoy local cafes, boutique shopping, and cultural street art. These activities not only foster personal discovery but also offer flexible scheduling and moderate costs.