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Cheap Flights from Charlottesville to Chicago
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Cheap Flights from Charlottesville to Chicago starting at S$ 292

Book one-way or return flights from Charlottesville to Chicago from as little as S$ 292. 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
        S$ 292S$ 430
        32% OFF
        32% OFF
        S$ 430S$ 292
      • CHO12:23
        4h 27m
        1 stop
        MDW15:50
        Wed, May 15|Charlottesville - Chicago|Delta Air Lines
        S$ 296S$ 430
        31% OFF
        31% OFF
        S$ 430S$ 296
      • CHO06:00
        6h 52m
        1 stop
        MDW11:52
        Wed, May 8|Charlottesville - Chicago|Delta Air Lines
        S$ 300S$ 430
        30% OFF
        30% OFF
        S$ 430S$ 300
      • CHO11:59
        8h 28m
        1 stop
        ORD19:27
        Thu, Jun 6|Charlottesville - Chicago|Delta Air Lines
        S$ 301
        S$ 301
      • CHO06:59
        7h 52m
        1 stop
        ORD13:51
        Thu, May 16|Charlottesville - Chicago|Delta Air Lines
        S$ 302
        S$ 302
      • CHO06:00
        5h 11m
        1 stop
        MDW10:11
        Sun, May 26|Charlottesville - Chicago|Delta Air Lines
        S$ 302
        S$ 302
      • CHO06:30
        5h 19m
        1 stop
        ORD10:49
        Mon, May 6|Charlottesville - Chicago|Delta Air Lines
        S$ 308
        S$ 308
      • CHO11:59
        7h 26m
        1 stop
        ORD18:25
        Fri, May 17|Charlottesville - Chicago|Delta Air Lines
        S$ 309
        S$ 309
      • CHO06:55
        2h 8m
        Direct
        ORD08:03
        Tue, May 21|Charlottesville - Chicago|United Airlines
        S$ 328
        S$ 328
      • CHO18:28
        6h 27m
        1 stop
        ORD23:55
        Mon, May 27|Charlottesville - Chicago|Delta Air Lines
        S$ 330
        S$ 330
      • CHO13:00
        3h 5m
        Direct
        CHI14:00
        Fri, May 3|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 lowest average weekly prices of the corresponding route on Trip.com.
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 S$ 292
United Airlines
From S$ 313
American Airlines
From S$ 373
ANA airlines

Find more flights and airlines

Alternative Routes from Charlottesville to Chicago

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
    S$ 292
  • Delta Air Lines
    CHO
    06:59
    7h 50m
    1 transfer
    ORD
    13:49
    Albemarle Airport - O'Hare International Airport
    Wed, May 15Delta Air Lines
    S$ 296
  • Delta Air Lines
    CHO
    06:59
    7h 50m
    1 transfer
    ORD
    13:49
    Albemarle Airport - O'Hare International Airport
    Wed, May 15Delta Air Lines
    S$ 296
    Find More Flights

Frequently Asked Questions

  • When to buy 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 is a flight from Charlottesville (CHO) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around S$ 589.

  • How long is a 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?

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 from Charlottesville to Chicago

Cheapest direct flight price

S$ 292

Cheapest return ticket price

S$ 339

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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