Cheap flights from Washington, D.C. to Chicago

Flights overview

Useful information for finding cheap flights from Washington, D.C. to Chicago and booking your next trip
Cheapest round-trip flights $78
Frontier Nonstop 3 hr Thu, Feb 5 — Mon, Feb 9
The cheapest round-trip flight from Washington, D.C. to Chicago is currently $78
Cheapest one-way flight $33
Frontier Nonstop 3 hr Thu, Mar 5
The cheapest one-way flight from Washington, D.C. to Chicago is currently $33
Last-minute weekend getaway $181
Spirit 1 stop 10 hr Sat, Jan 24 — Sun, Jan 25
The cheapest last-minute weekend getaway from Washington, D.C. to Chicago is currently $181
Cheapest business class flights $378
American Nonstop 3 hr Thu, Feb 19 — Sun, Feb 22
The cheapest business class round-trip flight from Washington, D.C. to Chicago is currently $378
Fastest flight 2 hr The fastest nonstop flight from Washington, D.C. to Chicago takes 2 hr
Nonstop flights Every day There are direct flights on this route every day.

When is the cheapest time to fly?

The cheapest month to fly from Washington, D.C. to Chicago is typically January. The most expensive month to fly is typically April.
January
Cheapest
Typical prices: $60–215
April
Most expensive
Typical prices: $150–225

Popular airlines from Washington, D.C. to Chicago

  • United
    Nonstop
    from $139
    Typical price: $155–325
    122 weekly nonstop flights
    BWI, DCA, IAD - ORD Every day
    1432 weekly connecting flights
    BWI, DCA, IAD - ORD Every day
  • Southwest
    Nonstop
    from $139
    Typical price: $165–330
    69 weekly nonstop flights
    BWI, DCA - MDW Every day
    3261 weekly connecting flights
    BWI, DCA, IAD - MDW, ORD Every day
  • American
    Nonstop
    from $158
    Typical price: $175–340
    70 weekly nonstop flights
    BWI, DCA - ORD Every day
    1175 weekly connecting flights
    BWI, DCA, IAD - ORD Every day
  • Delta
    from $177
    Typical price: $195–460
    1468 weekly connecting flights
    BWI, DCA, IAD - MDW, ORD Every day
  • Frontier
    Nonstop
    from $78
    Typical price: $115–260
    4 weekly nonstop flights
    BWI - ORD Every Mon, Thu, Fri, Sun
    81 weekly connecting flights
    BWI, DCA, IAD - MDW, ORD Every day
  • Alaska
    from $439
    Typical price: $520–1,200
    63 weekly connecting flights
    BWI, DCA, IAD - ORD Every day

Popular airports near Washington, D.C.

  • Ronald Reagan Washington National Airport (DCA)
    Washington United States 18 min 4 mi
  • Dulles International Airport (IAD)
    Washington United States 52 min 22 mi
  • Baltimore/Washington International Thurgood Marshall Airport (BWI) (BWI)
    Baltimore United States 49 min 27 mi
  • Philadelphia International Airport (PHL)
    Philadelphia United States 2 hr 20 min 116 mi

Popular airports near Chicago

  • Chicago O'Hare International Airport (ORD)
    Chicago United States 27 min 16 mi
  • Chicago Midway International Airport (MDW)
    Chicago United States 25 min 9 mi
  • Milwaukee Mitchell International Airport (MKE)
    Milwaukee United States 1 hr 24 min 75 mi
  • Indianapolis International Airport (IND)
    Indianapolis United States 2 hr 58 min 165 mi

Frequently asked questions about flying from Washington, D.C. to Chicago

The cheapest flights from Washington, D.C. to Chicago are usually in January. Typical ticket prices in January range from $60 to $215.
The cheapest round-trip flight from Washington, D.C. to Chicago recently found on Google Flights was with Frontier from $78. The cheapest one-way flight was with Frontier from $33.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest United flight from Washington, D.C. to Chicago is $139, flying from Feb 19 to Feb 23.
  • The cheapest Southwest flight from Washington, D.C. to Chicago is $139, flying from Feb 19 to Feb 23.
  • The cheapest American flight from Washington, D.C. to Chicago is $158, flying from Feb 19 to Feb 22.
  • The cheapest Delta flight from Washington, D.C. to Chicago is $177, flying from Feb 26 to Mar 2.
  • The cheapest Frontier flight from Washington, D.C. to Chicago is $78, flying from Feb 5 to Feb 9.
  • The cheapest Alaska flight from Washington, D.C. to Chicago is $439, flying from Feb 28 to Mar 2.
The cheapest round-trip flight from Washington, D.C. to Chicago starts at $78 from Thu, Feb 5 to Mon, Feb 9. The cheapest one-way flight starts at $33 and departs on Thu, Mar 5.
2 hr is the shortest flight time from Washington, D.C. to Chicago.
Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.
It's easy to use Google Flights to find the cheapest days to fly from Washington, D.C. to Chicago.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.
What counts as the best airline for your flights from Washington, D.C. to Chicago really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Washington, D.C. to Chicago.

In terms of nonstop flights, United is the most popular. United offers 122 nonstop flights and 1,432 connecting flights per week. United flies from Baltimore/Washington International Thurgood Marshall Airport (BWI) (BWI) , Ronald Reagan Washington National Airport (DCA) , Dulles International Airport (IAD) to Chicago O'Hare International Airport (ORD) .

In terms of flights, Southwest is the most popular. Southwest offers 69 nonstop flights and 3,261 connecting flights per week. Southwest flies from Baltimore/Washington International Thurgood Marshall Airport (BWI) (BWI) , Ronald Reagan Washington National Airport (DCA) , Dulles International Airport (IAD) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

Other popular airlines flying from Washington, D.C. to Chicago are:
  • American offers 70 nonstop flights and 1,175 connecting flights per week. American flies from Baltimore/Washington International Thurgood Marshall Airport (BWI) (BWI) , Ronald Reagan Washington National Airport (DCA) , Dulles International Airport (IAD) to Chicago O'Hare International Airport (ORD) .
  • Delta offers 1,468 connecting flights per week. Delta flies from Baltimore/Washington International Thurgood Marshall Airport (BWI) (BWI) , Ronald Reagan Washington National Airport (DCA) , Dulles International Airport (IAD) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
  • Frontier offers 4 nonstop flights and 81 connecting flights per week. Frontier flies from Baltimore/Washington International Thurgood Marshall Airport (BWI) (BWI) , Ronald Reagan Washington National Airport (DCA) , Dulles International Airport (IAD) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
  • Alaska offers 63 connecting flights per week. Alaska flies from Baltimore/Washington International Thurgood Marshall Airport (BWI) (BWI) , Ronald Reagan Washington National Airport (DCA) , Dulles International Airport (IAD) to Chicago O'Hare International Airport (ORD) .
The number of connecting flights refers to distinct flights with at least one stop between Washington, D.C. and Chicago.
The cheapest round-trip flight from Washington, D.C. to Chicago recently found on Google Flights was with Frontier from $78. The cheapest one-way flight was with Frontier from $33.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest United flight from Washington, D.C. to Chicago is $139, flying from Feb 19 to Feb 23.
  • The cheapest Southwest flight from Washington, D.C. to Chicago is $139, flying from Feb 19 to Feb 23.
  • The cheapest American flight from Washington, D.C. to Chicago is $158, flying from Feb 19 to Feb 22.
  • The cheapest Delta flight from Washington, D.C. to Chicago is $177, flying from Feb 26 to Mar 2.
  • The cheapest Frontier flight from Washington, D.C. to Chicago is $78, flying from Feb 5 to Feb 9.
  • The cheapest Alaska flight from Washington, D.C. to Chicago is $439, flying from Feb 28 to Mar 2.
Southwest, American, United and Frontier fly direct from Washington, D.C. to Chicago.
  • There are 122 United direct flights from Washington, D.C. to Chicago per week. Flights are available every day.
  • There are 69 Southwest direct flights from Washington, D.C. to Chicago per week. Flights are available every day.
  • There are 70 American direct flights from Washington, D.C. to Chicago per week. Flights are available every day.
  • There are 4 Frontier direct flights from Washington, D.C. to Chicago per week. Flights are available on Monday, Thursday, Friday and Sunday.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
The cheapest last-minute deal between Washington, D.C. and Chicago at price $181 is offered by Spirit from Sat, Jan 24 to Sun, Jan 25.
Southwest, American, United and Frontier fly direct from Washington, D.C. to Chicago.
  • There are 122 United direct flights from Washington, D.C. to Chicago per week. Flights are available every day.
  • There are 69 Southwest direct flights from Washington, D.C. to Chicago per week. Flights are available every day.
  • There are 70 American direct flights from Washington, D.C. to Chicago per week. Flights are available every day.
  • There are 4 Frontier direct flights from Washington, D.C. to Chicago per week. Flights are available on Monday, Thursday, Friday and Sunday.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
There are direct flights from Washington, D.C. to Chicago on a daily basis.
The cheapest direct (nonstop) round-trip flights between Washington, D.C. and Chicago start at $78 from Thu, Feb 5 to Mon, Feb 9 with Frontier.
It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Washington, D.C. to Chicago, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.
The cheapest business class round-trip flights between Washington, D.C. and Chicago start at $378 from Thu, Feb 19 to Sun, Feb 22 with American.
The cheapest economy class round-trip flights between Washington, D.C. and Chicago start at $78 from Thu, Feb 5 to Mon, Feb 9.
To book business class trips from Washington, D.C. to Chicago, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.
The best last-minute getaway deal for the next weekend between Washington, D.C. and Chicago starts at $181 from Sat, Jan 24 to Sun, Jan 25 with Spirit.
The cheapest last-minute deal between Washington, D.C. and Chicago at price $181 is offered by Spirit from Sat, Jan 24 to Sun, Jan 25.
To find last-minute flight deals from Washington, D.C. to Chicago, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.

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