Cheap flights from Vancouver to Chicago from C$ 142
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
YVR — CHI
16 Feb — 23 Feb1
Round-trip
1 adult
Economy
The best prices from Vancouver to Chicago are usually found in January or October, booked 66 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday
Cheap flight deals from Vancouver to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Vancouver (8CA) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 11 February 2025.
Explore the most affordable flight options available from Vancouver to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 11 February 2025.
Mon 5/57:00 a.m.YVR - ORD
1 stop7h 44mWestJet
Fri 9/55:30 p.m.ORD - YVR
1 stop7h 05mWestJet
Deal found 10/2C$ 281
Tue 11/39:05 a.m.YVR - ORD
1 stop19h 37mMultiple Airlines
Tue 18/37:47 a.m.ORD - YVR
1 stop16h 43mMultiple Airlines
Deal found 9/2C$ 304
Sat 1/35:30 p.m.YVR - MDW
1 stop10h 01mMultiple Airlines
Thu 6/38:44 p.m.MDW - YVR
2 stops21h 06mMultiple Airlines
Deal found 10/2C$ 380
Tue 11/36:30 a.m.YVR - ORD
Nonstop4h 14mAir Canada
Tue 18/38:06 p.m.ORD - YVR
Nonstop4h 46mAir Canada
Deal found 9/2C$ 383
Tue 11/36:30 a.m.YVR - ORD
Nonstop4h 14mUnited Airlines
Sat 15/37:00 a.m.ORD - YVR
1 stop10h 11mUnited Airlines
Deal found 11/2C$ 439
Wed 12/311:45 a.m.YVR - ORD
2 stops8h 00mDelta
Sat 15/37:50 a.m.ORD - YVR
2 stops12h 44mDelta
Deal found 10/2C$ 483
Sat 12/47:00 a.m.YVR - MDW
2 stops9h 33mDelta
Mon 21/410:20 a.m.MDW - YVR
2 stops10h 03mDelta
Deal found 10/2C$ 522
Tue 11/38:45 a.m.YVR - MDW
2 stops23h 35mPorter Airlines
Fri 14/311:15 a.m.MDW - YVR
2 stops11h 42mPorter Airlines
Deal found 11/2C$ 580
Wed 12/311:00 p.m.YVR - MDW
1 stop8h 09mWestJet
Sat 15/311:27 a.m.MDW - YVR
2 stops14h 34mWestJet
Deal found 10/2C$ 836
Best flights from Vancouver to Chicago
Discover carefully curated flight deals from Vancouver to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 11 February 2025.
Mon 3/36:30 a.m.YVR - ORD
1 stop7h 26mWestJet
Mon 10/34:45 p.m.ORD - YVR
1 stop9h 16mWestJet
Deal found 11/2C$ 275
Mon 10/36:30 a.m.YVR - ORD
1 stop7h 26mMultiple Airlines
Fri 14/37:59 p.m.ORD - YVR
1 stop28h 31mMultiple Airlines
Deal found 11/2C$ 304
Tue 11/36:30 a.m.YVR - ORD
Nonstop4h 14mAir Canada
Tue 18/38:06 p.m.ORD - YVR
Nonstop4h 46mAir Canada
Deal found 9/2C$ 383
Tue 11/36:30 a.m.YVR - ORD
Nonstop4h 14mUnited Airlines
Sat 15/37:00 a.m.ORD - YVR
1 stop10h 11mUnited Airlines
Deal found 11/2C$ 439
Wed 12/311:45 a.m.YVR - ORD
2 stops8h 00mDelta
Sat 15/37:50 a.m.ORD - YVR
2 stops12h 44mDelta
Deal found 10/2C$ 483
Tue 11/38:45 a.m.YVR - MDW
2 stops23h 35mPorter Airlines
Fri 14/311:15 a.m.MDW - YVR
2 stops11h 42mPorter Airlines
Deal found 11/2C$ 580
Sat 1/35:30 p.m.YVR - MDW
1 stop10h 01mMultiple Airlines
Thu 6/38:44 p.m.MDW - YVR
2 stops21h 06mMultiple Airlines
Deal found 10/2C$ 380
Sat 12/47:00 a.m.YVR - MDW
2 stops9h 33mDelta
Mon 21/410:20 a.m.MDW - YVR
2 stops10h 03mDelta
Deal found 10/2C$ 522
Wed 12/311:00 p.m.YVR - MDW
1 stop8h 09mWestJet
Sat 15/311:27 a.m.MDW - YVR
2 stops14h 34mWestJet
Deal found 10/2C$ 836
Direct flights from Vancouver to Chicago
Explore direct flight options from Vancouver to Chicago based on user searches, and compare prices and availability for your desired travel dates. Data last updated 11 February 2025.
Tue 11/36:30 a.m.YVR - ORD
Nonstop4h 14mAir Canada
Tue 18/38:06 p.m.ORD - YVR
Nonstop4h 46mAir Canada
Deal found 9/2C$ 383
Thu 10/48:30 a.m.YVR - ORD
Nonstop4h 13mMultiple Airlines
Sat 12/43:45 p.m.ORD - YVR
Nonstop4h 34mMultiple Airlines
Deal found 11/2C$ 410
Thu 6/36:30 a.m.YVR - ORD
Nonstop4h 14mUnited Airlines
Mon 10/38:06 p.m.ORD - YVR
Nonstop4h 46mUnited Airlines
Deal found 10/2C$ 602
Last-minute flights from Vancouver to Chicago
Discover last-minute flight deals from Vancouver to Chicago. Data last updated 11 February 2025 and is based on user searches.
Sun 16/27:00 a.m.YVR - ORD
1 stop15h 59mUnited Airlines
Thu 20/26:30 a.m.ORD - YVR
1 stop8h 49mUnited Airlines
Deal found 10/2C$ 536
Sun 16/27:01 a.m.YVR - ORD
1 stop14h 20mAeromexico
Wed 19/21:08 a.m.ORD - YVR
1 stop30h 07mAeromexico
Deal found 10/2C$ 9,457
Mon 17/28:10 a.m.YVR - ORD
1 stop6h 27mAir Canada
Mon 24/22:05 p.m.ORD - YVR
1 stop10h 10mAir Canada
Deal found 10/2C$ 579
Mon 17/28:30 a.m.YVR - ORD
2 stops23h 12mWestJet
Mon 24/26:15 a.m.ORD - YVR
2 stops19h 46mWestJet
Deal found 10/2C$ 1,119
Wed 19/28:00 a.m.YVR - MDW
2 stops14h 17mMultiple Airlines
Sat 22/27:00 a.m.MDW - YVR
1 stop16h 50mMultiple Airlines
Deal found 10/2C$ 503
Wed 19/211:00 p.m.YVR - ORD
2 stops14h 56mMultiple Airlines
Sat 22/211:35 a.m.ORD - YVR
1 stop28h 10mMultiple Airlines
Deal found 10/2C$ 555
Wed 19/25:20 p.m.YVR - ORD
2 stops17h 44mAlaska Airlines
Sat 22/24:05 p.m.ORD - YVR
2 stops9h 47mAlaska Airlines
Deal found 10/2C$ 741
Wed 19/28:45 a.m.YVR - MDW
2 stops25h 25mPorter Airlines
Sat 22/21:05 p.m.MDW - YVR
2 stops34h 29mPorter Airlines
Deal found 10/2C$ 1,852
Sat 1/35:30 p.m.YVR - MDW
1 stop10h 01mMultiple Airlines
Thu 6/38:44 p.m.MDW - YVR
2 stops21h 06mMultiple Airlines
Deal found 10/2C$ 380
Mon 3/36:30 a.m.YVR - ORD
1 stop7h 26mWestJet
Mon 10/34:45 p.m.ORD - YVR
1 stop9h 16mWestJet
Deal found 11/2C$ 275
Mon 3/35:20 p.m.YVR - ORD
2 stops17h 44mAlaska Airlines
Mon 10/37:00 p.m.ORD - YVR
2 stops19h 58mAlaska Airlines
Deal found 11/2C$ 572
Thu 6/37:00 a.m.YVR - MDW
2 stops8h 43mDelta
Mon 10/310:25 a.m.MDW - YVR
2 stops9h 58mDelta
Deal found 10/2C$ 609
One-way flights from Vancouver to Chicago
Search for one-way flight options from Vancouver to Chicago. Find affordable one-way fares based on user searches. Data last updated 11 February 2025.
Mon 10/36:30 a.m.YVR - ORD
1 stop7h 26mWestJet
Deal found 11/2C$ 142
Mon 24/33:55 p.m.YVR - ORD
1 stop12h 47mMultiple Airlines
Deal found 10/2C$ 181
Mon 24/38:35 p.m.YVR - MDW
2 stops17h 18mMultiple Airlines
Deal found 10/2C$ 192
Sat 12/48:30 a.m.YVR - ORD
Nonstop4h 13mUnited Airlines
Deal found 10/2C$ 232
Mon 3/36:30 a.m.YVR - ORD
Nonstop4h 14mAir Canada
Deal found 11/2C$ 234
Mon 3/35:20 p.m.YVR - ORD
2 stops17h 44mAlaska Airlines
Deal found 10/2C$ 254
Tue 8/47:25 p.m.YVR - MDW
2 stops11h 18mDelta
Deal found 11/2C$ 255
Sat 12/47:25 p.m.YVR - ORD
2 stops11h 47mDelta
Deal found 11/2C$ 255
Sun 23/36:30 a.m.YVR - ORD
Nonstop4h 14mLufthansa
Deal found 11/2C$ 344
Sun 16/36:00 a.m.YVR - MDW
1 stop26h 20mPorter Airlines
Deal found 9/2C$ 374
Sat 28/611:50 p.m.YVR - ORD
Nonstop4h 13mAmerican Airlines
Deal found 10/2C$ 390
Sun 4/511:00 p.m.YVR - MDW
1 stop21h 26mWestJet
Deal found 11/2C$ 461
Find flights from Vancouver to Chicago within your budget
Customize your flight search to find flights from Vancouver to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 11 February 2025.
Fly from
Any airport
Fly to
Any airport
Route
Depart
Return
Price
VancouverChicago
YVR - ORD
YVRORD
Vancouver Intl
Mon 5/5
7:00 a.m.-4:44 p.m.
1 stop7h 44m
Chicago O'Hare Intl
Fri 9/5
5:30 p.m.-10:35 p.m.
1 stop7h 05m
C$ 281
VancouverChicago
YVR - ORD
YVRORD
Vancouver Intl
Tue 11/3
9:05 a.m.-6:42 a.m.
1 stop19h 37m
Chicago O'Hare Intl
Tue 18/3
7:47 a.m.-10:30 p.m.
1 stop16h 43m
C$ 304
VancouverChicago
YVR - MDW
YVRMDW
Vancouver Intl
Sat 1/3
5:30 p.m.-5:31 a.m.
1 stop10h 01m
Chicago Midway
Thu 6/3
8:44 p.m.-3:50 p.m.
2 stops21h 06m
C$ 380
VancouverChicago
YVR - ORD
YVRORD
Vancouver Intl
Tue 11/3
6:30 a.m.-12:44 p.m.
Nonstop4h 14m
Chicago O'Hare Intl
Tue 18/3
11:35 a.m.-8:47 p.m.
1 stop11h 12m
C$ 383
VancouverChicago
YVR - ORD
YVRORD
Vancouver Intl
Tue 11/3
6:30 a.m.-12:44 p.m.
Nonstop4h 14m
Chicago O'Hare Intl
Sat 15/3
7:00 a.m.-3:11 p.m.
1 stop10h 11m
C$ 439
VancouverChicago
YVR - ORD
YVRORD
Vancouver Intl
Wed 12/3
11:45 a.m.-9:45 p.m.
2 stops8h 00m
Chicago O'Hare Intl
Sat 15/3
7:50 a.m.-6:34 p.m.
2 stops12h 44m
C$ 483
VancouverChicago
YVR - MDW
YVRMDW
Vancouver Intl
Sat 12/4
7:00 a.m.-6:33 p.m.
2 stops9h 33m
Chicago Midway
Mon 21/4
10:20 a.m.-6:23 p.m.
2 stops10h 03m
C$ 522
VancouverChicago
YVR - MDW
YVRMDW
Vancouver Intl
Sat 1/3
4:15 p.m.-10:20 a.m.
1 stop16h 05m
Chicago Midway
Thu 6/3
11:15 a.m.-1:04 a.m.
1 stop15h 49m
C$ 621
VancouverChicago
YVR - MDW
YVRMDW
Vancouver Intl
Wed 12/3
11:00 p.m.-9:09 a.m.
1 stop8h 09m
Chicago Midway
Sat 15/3
11:27 a.m.-12:01 a.m.
2 stops14h 34m
C$ 836
VancouverChicago
YVR - ORD
YVRORD
Vancouver Intl
Mon 24/3
6:30 a.m.-3:56 p.m.
1 stop7h 26m
C$ 145
Flights are sorted by cheapest round-trip flights first.
Deals found on 10/2
Showing 1-10 of 21 results
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Best time to book a flight from Vancouver to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Vancouver with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Travel insights for flights from Vancouver to Chicago
Get recent, data-driven insights about flights from Vancouver to Chicago including ideal travel times, pricing trends, and more.
How far ahead should I book a flight from Vancouver to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Vancouver to Chicago. Price data was last updated on 7 February 2025.
To ensure you get the cheapest price possible for a flight from Vancouver to Chicago, you should look to book at least 66 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Vancouver to Chicago?
Currently, January is the cheapest month in which you can book a flight from Vancouver to Chicago (average of C$ 261). Flying from Vancouver to Chicago in March is currently the most expensive (average of C$ 355). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from YVR to CHI?
Find hourly flight availability from Vancouver to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 11 February 2025.
When flying from Vancouver to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 36% versus a flight at noon.
What is the cheapest day to fly from Vancouver to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Vancouver to Chicago. Price data was last updated on 10 November 2024.
Travelers seeking maximum savings on their Vancouver to Chicago flight should consider departing on Thursday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Vancouver to Chicago
Explore weekly flight availability from Vancouver to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 11 February 2025.
The most flights from 8CA to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (2 on average).
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 11 February 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Delta and Porter Airlines from Vancouver to Chicago to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.