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Find Charlottesville to Chicago flights starting at CAD 294.

Book one-way or return flights from Charlottesville to Chicago from as little as CAD 294. Choose from the popular airlines below and book your flight today!

  • One way
  • Round-trip
      • CHO06:00
        4h 10m
        1 stop
        MDW09:10
        Sun, May 5|Charlottesville - Chicago|Delta Air Lines
        CAD 294CAD 432
        32% OFF
        32% OFF
        CAD 432CAD 294
      • CHO12:23
        4h 27m
        1 stop
        MDW15:50
        Wed, May 15|Charlottesville - Chicago|Delta Air Lines
        CAD 297CAD 432
        31% OFF
        31% OFF
        CAD 432CAD 297
      • CHO06:00
        6h 52m
        1 stop
        MDW11:52
        Wed, May 8|Charlottesville - Chicago|Delta Air Lines
        CAD 302CAD 432
        30% OFF
        30% OFF
        CAD 432CAD 302
      • CHO11:59
        8h 28m
        1 stop
        ORD19:27
        Thu, Jun 6|Charlottesville - Chicago|Delta Air Lines
        CAD 302
        CAD 302
      • CHO06:59
        7h 52m
        1 stop
        ORD13:51
        Thu, May 16|Charlottesville - Chicago|Delta Air Lines
        CAD 303
        CAD 303
      • CHO06:00
        5h 11m
        1 stop
        MDW10:11
        Sun, May 26|Charlottesville - Chicago|Delta Air Lines
        CAD 303
        CAD 303
      • CHO06:30
        5h 19m
        1 stop
        ORD10:49
        Mon, May 6|Charlottesville - Chicago|Delta Air Lines
        CAD 309
        CAD 309
      • CHO11:59
        7h 26m
        1 stop
        ORD18:25
        Fri, May 17|Charlottesville - Chicago|Delta Air Lines
        CAD 310
        CAD 310
      • CHO06:55
        2h 8m
        Direct
        ORD08:03
        Tue, May 21|Charlottesville - Chicago|United Airlines
        CAD 330
        CAD 330
      • CHO18:28
        6h 27m
        1 stop
        ORD23:55
        Mon, May 27|Charlottesville - Chicago|Delta Air Lines
        CAD 332
        CAD 332
      • CHO13:00
        3h 5m
        Direct
        CHI14:00
        Mon, May 6|Charlottesville - Chicago|Delta Air Lines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Searching for the best last minute flight from Charlottesville to Chicago? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Charlottesville to Chicago. Stay updated on price trends and snag the best deals for your upcoming trip.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Find Cheapest Airlines Flying from Charlottesville to Chicago

View airlines operating flights from Charlottesville to Chicago. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Delta Air Lines
From CAD 294
United Airlines
From CAD 314
American Airlines
From CAD 375
ANA airlines

Find more flights and airlines

Alternative Routes for Charlottesville to Chicago Flights

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Charlottesville to Chicago.

  • Cheapest
    Delta Air Lines
    CHO
    06:00
    4h 10m
    1 transfer
    MDW
    09:10
    Albemarle Airport - Midway International Airport
    Sun, May 5Delta Air Lines
    CAD 294
  • Delta Air Lines
    CHO
    06:59
    7h 50m
    1 transfer
    ORD
    13:49
    Albemarle Airport - O'Hare International Airport
    Wed, May 15Delta Air Lines
    CAD 297
  • Delta Air Lines
    CHO
    06:59
    7h 50m
    1 transfer
    ORD
    13:49
    Albemarle Airport - O'Hare International Airport
    Wed, May 15Delta Air Lines
    CAD 297
    Find More Flights

How do I find the cheapest flights?

  • When are flight tickets from Charlottesville (CHO) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Charlottesville to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much are flights from Charlottesville (CHO) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around CAD 602.

  • How long is the flight from Charlottesville (CHO) to Chicago (CHI)?

    It takes about 2 hours 6 minutes to fly from Charlottesville (CHO) to Chicago (CHI).

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.

  • What are the most popular airlines that fly from Charlottesville (CHO) to Chicago (CHI)?

    Airlines with flights from Charlottesville (CHO) to Chicago (CHI): United Airlines.

  • What's the most popular airline for direct flights from Charlottesville (CHO) to Chicago (CHI)?

    United Airlines operates 3 direct flights from Charlottesville (CHO) to Chicago (CHI).

  • How many airports in Chicago (CHI)?

How to find a cheap flight from Charlottesville to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Charlottesville to Chicago. Book your flights at the right time and save more.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com
Flight Information for Charlottesville to Chicago Flights

Cheapest direct flight price

CAD 293

Cheapest return ticket price

CAD 340

Cheapest month

January

Peak season for travel

November

Flight distance

885.19km

Average flight time

2 hours 6 minutes

Popular airline

American Airlines

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