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Flights from Washington D.C. to Chicago
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Book flight tickets from Washington D.C. to Chicago starting at €45

Whether you’re going for a one-way or round-trip to Chicago, we’ve got you covered! Check out these different flight options from Washington D.C. below.

  • One way
  • Round-trip
      • Cheapest nonstop
        DCA06:05
        2h 10m
        Nonstop
        MDW07:15
        Sat, Jan 11|Washington D.C. - Chicago|Southwest Airlines
        €65€134
        51% OFF
        51% OFF
        €134€65

        Choose Southwest Airlines flights from Washington D.C. to Chicago. The one-way direct flight with Southwest Airlines departs from Ronald Reagan Washington National Airport on Sat, Jan 11, arriving at Midway International Airport. One-way ticket prices start from €65 including taxes and charges.

      • DCA06:59
        2h 21m
        Nonstop
        ORD08:20
        Tue, Feb 18|Washington D.C. - Chicago|American Airlines
        €81€134
        40% OFF
        40% OFF
        €134€81

        Choose American Airlines flights from Washington D.C. to Chicago. The one-way direct flight with American Airlines departs from Ronald Reagan Washington National Airport on Tue, Feb 18, arriving at O'Hare International Airport. One-way ticket prices start from €81 including taxes and charges.

      • IAD09:44
        13h 20m
        1 stop
        MDW22:04
        Sat, Feb 15|Washington D.C. - Chicago|Frontier Airlines
        €45€134
        66% OFF
        66% OFF
        €134€45

        Choose Frontier Airlines flights from Washington D.C. to Chicago. The one-way connecting flight with Frontier Airlines departs from Washington Dulles International Airport on Sat, Feb 15, arriving at Midway International Airport. One-way ticket prices start from €45 including taxes and charges.

      • IAD20:11
        12h 17m
        1 stop
        ORD07:28
        Tue, Feb 18|Washington D.C. - Chicago|Frontier Airlines
        €46
        €46

        Choose Frontier Airlines flights from Washington D.C. to Chicago. The one-way connecting flight with Frontier Airlines departs from Washington Dulles International Airport on Tue, Feb 18, arriving at O'Hare International Airport. One-way ticket prices start from €46 including taxes and charges.

      • IAD13:17
        6h 49m
        1 stop
        MDW19:06
        Wed, Feb 5|Washington D.C. - Chicago|Frontier Airlines
        €47
        €47

        Choose Frontier Airlines flights from Washington D.C. to Chicago. The one-way connecting flight with Frontier Airlines departs from Washington Dulles International Airport on Wed, Feb 5, arriving at Midway International Airport. One-way ticket prices start from €47 including taxes and charges.

      • IAD09:44
        7h 47m
        1 stop
        ORD16:31
        Sat, Feb 22|Washington D.C. - Chicago|Frontier Airlines
        €47
        €47

        Choose Frontier Airlines flights from Washington D.C. to Chicago. The one-way connecting flight with Frontier Airlines departs from Washington Dulles International Airport on Sat, Feb 22, arriving at O'Hare International Airport. One-way ticket prices start from €47 including taxes and charges.

      • IAD11:19
        13h 10m
        1 stop
        MDW23:29
        Sat, Feb 8|Washington D.C. - Chicago|Frontier Airlines
        €49
        €49

        Choose Frontier Airlines flights from Washington D.C. to Chicago. The one-way connecting flight with Frontier Airlines departs from Washington Dulles International Airport on Sat, Feb 8, arriving at Midway International Airport. One-way ticket prices start from €49 including taxes and charges.

      • IAD08:15
        7h 43m
        1 stop
        MDW14:58
        Mon, Jan 13|Washington D.C. - Chicago|Frontier Airlines
        €49
        €49

        Choose Frontier Airlines flights from Washington D.C. to Chicago. The one-way connecting flight with Frontier Airlines departs from Washington Dulles International Airport on Mon, Jan 13, arriving at Midway International Airport. One-way ticket prices start from €49 including taxes and charges.

      • IAD13:17
        5h 40m
        1 stop
        MDW17:57
        Wed, Jan 15|Washington D.C. - Chicago|Frontier Airlines
        €49
        €49

        Choose Frontier Airlines flights from Washington D.C. to Chicago. The one-way connecting flight with Frontier Airlines departs from Washington Dulles International Airport on Wed, Jan 15, arriving at Midway International Airport. One-way ticket prices start from €49 including taxes and charges.

      • DCA18:00
        7h 17m
        1 stop
        MDW00:17
        Mon, Jan 27|Washington D.C. - Chicago|Frontier Airlines
        €49
        €49

        Choose Frontier Airlines flights from Washington D.C. to Chicago. The one-way connecting flight with Frontier Airlines departs from Ronald Reagan Washington National Airport on Mon, Jan 27, arriving at Midway International Airport. One-way ticket prices start from €49 including taxes and charges.

      • WAS01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Tue, Jan 14|Washington D.C. - Chicago|Southwest Airlines
        Find More Flights
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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Find the best time to fly from Washington D.C. to Chicago

These price trend charts carefully monitor and predict how flight prices from Washington D.C. to Chicago will change. Keep a close eye on them to understand when the best time to buy your tickets is.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Airlines Flying from Washington D.C. to Chicago

Compare prices from various providers below to understand which option best suits your travel needs, before enjoying a comfortable journey with a trusted airline from Washington D.C. to Chicago.

Southwest Airlines
From €65
Jetblue Airways
From €78
Delta Air Lines
From €87
Frontier Airlines
From €107
United Airlines
From €109
Sun Country Airlines
From €133
American Airlines
From €297

Find more flights and airlines

Alternative Routes from Washington D.C. to Chicago

Searching for potential routes that might be cheaper and faster? There are a few alternative ways to get to Chicago from Washington D.C. which could help you save money and time.

  • Cheapest
    Frontier Airlines
    IAD
    09:44
    13h 20m
    1 transfer
    MDW
    22:04
    Washington Dulles International Airport - Midway International Airport
    Sat, Feb 15Frontier Airlines
    €45
  • Frontier Airlines
    DCA
    18:00
    7h 17m
    1 transfer
    MDW
    00:17
    Ronald Reagan Washington National Airport - Midway International Airport
    Mon, Jan 27Frontier Airlines
    €49
  • Frontier Airlines
    IAD
    16:42
    7h 0m
    1 transfer
    ORD
    22:42
    Washington Dulles International Airport - O'Hare International Airport
    Thu, Jan 9Frontier Airlines
    €107
  • Frontier Airlines
    IAD
    16:42
    7h 0m
    1 transfer
    ORD
    22:42
    Washington Dulles International Airport - O'Hare International Airport
    Thu, Jan 9Frontier Airlines
    €107
    Find More Flights

FAQ

  • When are flight tickets from Washington D.C. (WAS) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Washington D.C. to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Washington D.C. (WAS) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around €206.

  • How long does it take to fly from Washington D.C. (WAS) to Chicago (CHI) and what is the distance?

    It takes around 2 hours 13 minutes to fly from Washington D.C. (WAS) 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 25 km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.

  • What are the most popular airlines that fly from Washington D.C. (WAS) to Chicago (CHI)?

    Airlines with flights from Washington D.C. (WAS) to Chicago (CHI): Southwest Airlines, Air New Zealand, All Nippon Airways, United Airlines, Austrian Airlines, Japan Airlines, British Airways and Air Canada.

How to find a cheap flight from Washington D.C. to Chicago

Understanding the common pitfalls when booking your flight tickets can help you save massively when it comes time to fly. We’ve listed our six essential steps to keep in mind when you’re booking flight tickets to help you find the best price.
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 Washington D.C. to Chicago

Cheapest nonstop flight price€45
Cheapest round-trip ticket price€135
Off-season for travelNovember
Peak season for travelApril
Flight distance957.18 km
Average flight time2 hours 13 minutes
Popular airlineUnited Airlines

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