DCA - CHI

$97 Find Cheap Flights from Reagan Washington National Airport to Chicago - Compare and Save

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Everything you should know

Cheapest round-trip
$208
Typical prices: $270-$431
Frontier
Sat 11/10Sat 11/24
DCA - ORD • 1 stop
Cheapest non-stop
$211
Typical prices: $270-$432
American Airlines
Wed 11/7Fri 11/9
DCA - ORD • Non-stop
Nonstop flights
You can fly direct with American Airlines, United Airlines and Southwest. Average duration is 2h 22m
Direct flights
+1
Direct flights
+1
Top routes
Cheapest • 1% average savings
Most popular
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 26 weeks in advance save around 53% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 13% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $208 (round-trip)
Shortest trip • 4h 07m (one-way)
Insights
Insights
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Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Reagan-National to Chicago (DCA-CHI)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Reagan-National to Chicago

Tue, Nov 10 - Tue, Nov 24
Frontier Logo
7:00 am - 12:21 amDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
18h 21m1 stop Denver Intl
Frontier Logo
6:40 am - 9:55 pmORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
14h 15m1 stop Denver Intl
$208Frontier
Fri, Oct 30 - Sat, Oct 31
Frontier Logo
6:00 pm - 12:21 amDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
7h 21m1 stop Denver Intl
Frontier Logo
6:30 am - 4:47 pmORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
9h 17m1 stop Denver Intl
$208Frontier
Thu, Nov 5 - Tue, Nov 10
United Airlines Logo
6:25 am - 7:43 amDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
2h 18mnonstop
United Airlines Logo
9:00 am - 12:03 pmORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
2h 03mnonstop
$211United Airlines
Thu, Dec 17 - Mon, Dec 21
United Airlines Logo
7:35 am - 9:00 amDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
2h 25mnonstop
United Airlines Logo
12:29 pm - 3:34 pmORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
2h 05mnonstop
$211United Airlines
Tue, Nov 3 - Tue, Nov 10
Southwest Logo
1:00 pm - 2:10 pmDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
2h 10mnonstop
Southwest Logo
8:35 pm - 11:20 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
1h 45mnonstop
$211Southwest
Mon, Nov 2 - Wed, Nov 4
Southwest Logo
10:45 am - 11:50 amDCA  Washington, D.C. Reagan-National-MDW Chicago Midway
2h 05mnonstop
Southwest Logo
1:30 pm - 4:15 pmMDW  Chicago Midway-DCA Washington, D.C. Reagan-National
1h 45mnonstop
$211Southwest
Sat, Jan 23 - Wed, Jan 27
American Airlines Logo
11:39 am - 1:15 pmDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
2h 36mnonstop
American Airlines Logo
9:56 am - 12:59 pmORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
2h 03mnonstop
$211American Airlines
Wed, Oct 28 - Sat, Oct 31
American Airlines Logo
3:47 pm - 5:17 pmDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
2h 30mnonstop
American Airlines Logo
6:59 am - 10:06 amORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
2h 07mnonstop
$211American Airlines
Sat, Nov 7 - Mon, Nov 9
Multiple Airlines Logo
6:00 pm - 12:21 amDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
7h 21m1 stop Denver Intl
Multiple Airlines Logo
7:00 am - 9:59 amORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
25h 59m1 stop Fort Lauderdale
$223Multiple Airlines
Sat, Nov 7 - Mon, Nov 9
Multiple Airlines Logo
6:00 pm - 12:21 amDCA  Washington, D.C. Reagan-National-ORD Chicago O'Hare Intl
7h 21m1 stop Denver Intl
Multiple Airlines Logo
7:00 am - 9:59 amORD  Chicago O'Hare Intl-DCA Washington, D.C. Reagan-National
25h 59m1 stop Fort Lauderdale
$223Multiple Airlines
Booking Insights

Price, demand and travel trends for Washington, D.C. Reagan-National Airport to Chicago flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Washington, D.C. Reagan-National Airport to Chicago?

Round-trip flights from Washington, D.C. Reagan-National Airport to Chicago typically range from $270 to $431. The lowest price found in the past 5 days was $208, on Frontier.

What is the cheapest Washington, D.C. Reagan-National Airport to Chicago flight route?

There's little price difference between Washington, D.C. Reagan-National Airport to Chicago routes. They average around $329 round-trip, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Washington, D.C. Reagan-National Airport to Chicago?

Based on deals KAYAK users found in the last 12 months, Saturday is the cheapest day of the week to fly from Washington, D.C. Reagan-National Airport to Chicago. It’s 9% cheaper than the average day, while Monday is the most expensive, with prices 10% higher.

What’s the cheapest month to fly from Washington, D.C. Reagan-National Airport to Chicago?

•September is the cheapest month to fly from Washington, D.C. Reagan-National Airport to Chicago at $287 round-trip.
•November ($382) and June ($364) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 33% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Washington, D.C. Reagan-National Airport to Chicago the cheapest?

Flights from Washington, D.C. Reagan-National Airport to Chicago are cheapest 26 weeks before departure. Booking in this window typically costs about 53% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from Reagan-National to Chicago

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Ramsey Qubein

Ramsey Qubein

Expert on DCA

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Key details for Washington, D.C. Reagan-National Airport to Chicago flights

Low season

January

Cheapest flight

$97
Beat the crowds with an average 62% drop in travelers.
The most popular month to fly with an average 47% increase in travelers.
One-way flight from Washington, D.C. Reagan-National Airport to Chicago O'Hare Intl Airport

When to book flights from Reagan-National to Chicago

Are your dates flexible? Find out the best times to travel from Reagan-National to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Washington, D.C. Reagan-National Airport to Chicago flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Washington, D.C. Reagan-National Airport to Chicago?

    These are the earliest and latest flight times available from Washington, D.C. Reagan-National Airport to Chicago:

    • Earliest: departs at 5:54 am and lands at 8:16 am
    • Latest: departs at 10:25 pm and lands at 12:47 am.

    The flight takes about 2h 22m.

  • What cabin classes can I book on flights from Washington, D.C. Reagan-National Airport to Chicago?

    Three cabin classes are available on flights from Washington, D.C. Reagan-National Airport to Chicago:

    • Economy Class
    • Business Class
    • First Class

  • How long is a flight from Washington, D.C. Reagan-National Airport to Chicago?

    A nonstop flight from Washington, D.C. Reagan-National Airport to Chicago takes 2h 22m, covering 594 miles.

  • Do I need a passport to fly from Washington, D.C. Reagan-National Airport to Chicago?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Washington, D.C. Reagan-National Airport to Chicago flight?

    Round-trip flights from Washington, D.C. Reagan-National Airport to Chicago range from $270 to $431, with an average of $328 over the past 12 months. Anything below $270 counts as a good deal.

  • How expensive are last-minute Washington, D.C. Reagan-National Airport to Chicago flights?

    Last-minute fares on this route (booked within two weeks of departure) run 74% above the $328 route average. Book 26 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Washington, D.C. Reagan-National Airport to Chicago?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $208 round-trip via New York John F Kennedy Intl (JFK), compared to $328 for nonstop.

  • What is the standard checked-bag allowance on flights from Washington, D.C. Reagan-National Airport to Chicago?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • How are flight departures from Washington, D.C. Reagan-National Airport to Chicago spread across the day?

    Morning is the busiest departure period on Washington, D.C. Reagan-National Airport to Chicago flights, with 45% of flights leaving in that window. Evening departures account for 27%, afternoon flights for 25%, and night flights for 3%.

  • Have flight prices from Washington, D.C. Reagan-National Airport to Chicago changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $208 to $1,372. That means the highest observed fare was about 7x higher than the lowest one.

  • Which airlines offer Wi-Fi on Washington, D.C. Reagan-National Airport to Chicago flights?

    Two airlines offer in-flight Wi-Fi on Washington, D.C. Reagan-National Airport to Chicago flights:

    • American Airlines
    • JetBlue

    Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

  • How are flight prices from Washington, D.C. Reagan-National Airport to Chicago looking right now?

    One-way fares from Washington, D.C. Reagan-National Airport to Chicago are currently lower than usual. Average one-way flight prices are about $107, which is 54% below the typical average for this route.

  • What car rental options are available in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Ace
    • Dollar

    Near Chicago Midway Airport (MDW) — daily rates from around $32:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

    Near Chicago Greater Rockford Airport (RFD) — daily rates from around $28:

    • Alamo
    • Enterprise Rent-A-Car
    • Budget
    • Avis
    • National

  • Which airports can I use when flying from Washington, D.C. Reagan-National Airport to Chicago?

    Flights from Washington, D.C. Reagan-National Airport to Chicago usually depart from Washington, D.C. Reagan-National (DCA) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • Which airports do connecting flights from Washington, D.C. Reagan-National Airport to Chicago pass through?

    One-stop flights from Washington, D.C. Reagan-National Airport to Chicago most commonly connect through:

    • Boston Logan Intl (BOS) - 44% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) - 18% of one-stop connections
    • Denver Intl (DEN) - 11% of one-stop connections
    • New York John F Kennedy Intl (JFK) - 11% of one-stop connections

  • Can I save money by using flexible dates for flights from Washington, D.C. Reagan-National Airport to Chicago?

    Yes. Flexible dates can save you up to 18% on flights from Washington, D.C. Reagan-National Airport to Chicago. Saturday is the cheapest departure day at $299 round-trip on average, while Monday is the most expensive at $362, a difference of $63.

    Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • What airlines fly from Washington, D.C. Reagan-National Airport to Chicago?

    3 airlines operate flights between Washington, D.C. Reagan-National Airport and Chicago. The airlines offering nonstop flights on this route include:

    • American Airlines
    • United Airlines
    • Southwest

  • How much time can I save by choosing a different layover airport from Washington, D.C. Reagan-National Airport to Chicago?

    Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 4h 07m, compared with 4h 10m via Lambert-St Louis (STL) and 4h 44m via Chicago O'Hare Intl (ORD).

  • What is the time difference between Washington, D.C. Reagan-National Airport and Chicago?

    Chicago is 1 hour behind Washington, D.C. Reagan-National Airport (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Chicago?

    Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Washington, D.C. Reagan-National Airport to Chicago flights?

    Among airlines operating Washington, D.C. Reagan-National Airport to Chicago flights:

    • United Airlines: offers extra legroom; offers free seat selection
    • American Airlines: offers extra legroom; offers free seat selection
    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Washington, D.C. Reagan-National Airport to Chicago flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • United Airlines: a cabin bag and a checked bag in Economy Class
    • American Airlines: a cabin bag and a checked bag in Economy Class
    • Southwest: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Washington, D.C. Reagan-National Airport to Chicago flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Saturday departure and avoid flying on Monday. On this route, Saturday flights average $299, about $63 less than Monday fares (17% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 26 weeks before you fly. On this route, that window historically saves about 53% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Washington, D.C. Reagan-National Airport to Chicago trip for September. Fares historically average $287 round-trip in that month - typically $95 less than the most expensive month, which is November (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through New York John F Kennedy Intl Airport (JFK) can be cheaper than flying direct. The cheapest layover option averages $208 round-trip on this route - about $120 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel

Prefer to fly direct from Reagan Washington National Airport to Chicago?

 
Find which airlines fly direct from Washington, D.C. Reagan-National Airport to Chicago, which days they fly and book direct flights.

Direct departures

Washington, D.C. Reagan-National to Chicago

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Direct returns

Chicago to Washington, D.C. Reagan-National

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

More options for your flight from Reagan-National to Chicago

Complete your trip to Chicago with a hotel stay or car rental