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Flight Deals from Reagan Washington National Airport to Chicago from $99

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Stops

  • Nonstop
    from $229
  • Up to 1 stop
    $197

Airlines

  • American Airlines
    $229
  • Delta Air Lines
    $197
  • Frontier Airlines
    $199
  • JetBlue
    $219
  • Southwest Airlines
    $295
  • United Airlines
    $229

Cabin Class

  • Economy
    $197

Departure Airports

  • Reagan Washington National Airport
    $197

Arrival Airports

  • Chicago Midway Airport
    $198
  • Chicago O Hare Airport
    $197

Layover Airports

  • Charlotte Douglas International Airport
    $284
  • Cleveland Hopkins International Airport
    $320
  • Denver International Airport
    $199
  • Detroit Metropolitan Airport
    $197
  • General Edward Lawrence Logan International Airport
    $219
  • Hartsfield Jackson Atlanta International Airport
    $197
  • Indianapolis International Airport
    $342
  • John Glenn Columbus International Airport
    $275
  • Minneapolis-St Paul International/Wold-Chamberlain Airport
    $237
  • New York John F Kennedy Airport
    $219
  • New York LaGuardia Airport
    $270
  • Newark Liberty Airport
    $298
  • Orlando International Airport
    $219
  • Pittsburgh International Airport
    $299
  • Raleigh Durham International Airport
    $279
  • St Louis Lambert International Airport
    $318
  • Will Rogers World Airport
    $318

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On average save $240 per traveler
Delta Air Lines Logo
Delta Air Lines

05/24/25

DCA
4h
DTW

05/24/25

ORD
Delta Air Lines Logo
Delta Air Lines

05/31/25

ORD
4h 45m
DTW

05/31/25

DCA
$197
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/25/25

DCA
3h 18m
DTW

05/25/25

ORD
Delta Air Lines Logo
Delta Air Lines

05/29/25

ORD
5h 38m
ATL

05/29/25

DCA
$197
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/29/25

DCA
2h 48m
DTW

05/29/25

MDW
Delta Air Lines Logo
Delta Air Lines

05/31/25

MDW
4h 45m
DTW

05/31/25

DCA
$198
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/19/25

DCA
6h 8m
DEN

05/19/25

MDW
Frontier Airlines Logo
Frontier Airlines

05/22/25

MDW
6h 8m
ATL

05/22/25

DCA
$199
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

05/21/25

DCA
6h 51m
BOS

05/21/25

ORD
JetBlue Logo
JetBlue

05/28/25

ORD
6h 55m
JFK

05/28/25

DCA
$219
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/24/25

DCA
10h 52m
DEN

05/24/25

ORD
Frontier Airlines Logo
Frontier Airlines

05/26/25

ORD
20h 1m
MCO

05/27/25

DCA
$219
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

05/20/25

DCA
6h 51m
BOS

05/20/25

ORD
JetBlue Logo
JetBlue

05/27/25

ORD
6h 55m
JFK

05/27/25

DCA
$219
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/24/25

DCA
1h 16m
Direct

05/24/25

ORD
United Airlines Logo
United Airlines

05/31/25

ORD
3h 3m
Direct

05/31/25

DCA
$229
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/25/25

DCA
1h 19m
Direct

05/25/25

ORD
United Airlines Logo
United Airlines

05/27/25

ORD
3h 7m
Direct

05/27/25

DCA
$229
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/25/25

DCA
1h 13m
Direct

05/25/25

ORD
American Airlines Logo
American Airlines

05/29/25

ORD
3h 1m
Direct

05/29/25

DCA
$229
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/24/25

DCA
1h 11m
Direct

05/24/25

ORD
American Airlines Logo
American Airlines

05/25/25

ORD
2h 54m
Direct

05/25/25

DCA
$230
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

06/07/25

DCA
3h 51m
DTW

06/07/25

MDW
Delta Air Lines Logo
Delta Air Lines

06/10/25

MDW
7h 56m
MSP

06/10/25

DCA
$237
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/03/25

DCA
3h 49m
LGA

06/03/25

ORD
American Airlines Logo
American Airlines

06/04/25

ORD
3h 1m
Direct

06/04/25

DCA
$270
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/25/25

DCA
1h 14m
Direct

05/25/25

ORD
American Airlines Logo
American Airlines

05/27/25

ORD
5h 57m
CMH

05/27/25

DCA
$275
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/21/25

DCA
3h 53m
RDU

05/21/25

ORD
American Airlines Logo
American Airlines

05/30/25

ORD
3h 1m
Direct

05/30/25

DCA
$279
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/29/25

DCA
1h 20m
Direct

05/29/25

ORD
American Airlines Logo
American Airlines

06/01/25

ORD
5h 3m
CLT

06/01/25

DCA
$284
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/31/25

DCA
1h 13m
Direct

05/31/25

ORD
American Airlines Logo
American Airlines

06/07/25

ORD
5h 34m
CLT

06/07/25

DCA
$284
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/02/25

DCA
5h 52m
LGA

06/02/25

ORD
American Airlines Logo
American Airlines

06/10/25

ORD
3h 19m
Direct

06/10/25

DCA
$294
Free cancellation within 83 hours of booking
Southwest Airlines Logo
Southwest Airlines

05/18/25

DCA
55m
Direct

05/18/25

MDW
Southwest Airlines Logo
Southwest Airlines

05/20/25

MDW
2h 50m
Direct

05/20/25

DCA
$295
Free cancellation within 83 hours of booking
Southwest Airlines Logo
Southwest Airlines

05/18/25

DCA
1h
Direct

05/18/25

MDW
Southwest Airlines Logo
Southwest Airlines

05/20/25

MDW
2h 50m
Direct

05/20/25

DCA
$298
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/03/25

DCA
3h 45m
EWR

06/03/25

ORD
United Airlines Logo
United Airlines

06/06/25

ORD
3h 3m
Direct

06/06/25

DCA
$298
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/22/25

DCA
5h 50m
PIT

05/22/25

ORD
American Airlines Logo
American Airlines

05/28/25

ORD
2h 47m
Direct

05/28/25

DCA
$299
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/23/25

DCA
5h 50m
PIT

05/23/25

ORD
American Airlines Logo
American Airlines

05/24/25

ORD
2h 58m
Direct

05/24/25

DCA
$304
Free cancellation within 83 hours of booking
Southwest Airlines Logo
Southwest Airlines

05/18/25

DCA
7h 45m
CMH

05/18/25

MDW
Southwest Airlines Logo
Southwest Airlines

05/20/25

MDW
2h 50m
Direct

05/20/25

DCA
$308
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/31/25

DCA
1h 14m
Direct

05/31/25

ORD
United Airlines Logo
United Airlines

06/07/25

ORD
6h 25m
EWR

06/07/25

DCA
$317
Free cancellation within 83 hours of booking
Southwest Airlines Logo
Southwest Airlines

05/18/25

DCA
4h 40m
OKC

05/18/25

MDW
Southwest Airlines Logo
Southwest Airlines

05/20/25

MDW
8h
STL

05/20/25

DCA
$318
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/31/25

DCA
4h 35m
RDU

05/31/25

ORD
American Airlines Logo
American Airlines

06/01/25

ORD
5h 3m
CLT

06/01/25

DCA
$319
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/20/25

DCA
2h 42m
CLE

05/20/25

ORD
American Airlines Logo
American Airlines

05/21/25

ORD
8h 24m
CLT

05/21/25

DCA
$320
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/22/25

DCA
5h 50m
PIT

05/22/25

ORD
American Airlines Logo
American Airlines

05/28/25

ORD
4h 16m
CLE

05/28/25

DCA
$335
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

06/01/25

DCA
5h 50m
IND

06/01/25

ORD
American Airlines Logo
American Airlines

06/08/25

ORD
2h 50m
Direct

06/08/25

DCA
$342
Free cancellation within 83 hours of booking

Top Deals on flights from Reagan Washington National Airport to Chicago

Washington, US (WAS) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

May 28

DCA
2h 48m
DTW

May 28

MDW

as low as

$99

Washington, US (WAS) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

Jun 7

DCA
7h 53m
DEN

Jun 7

MDW

as low as

$103

Washington, US (WAS) - Chicago, US (CHI)

JetBlue Logo
JetBlue

Jun 3

DCA
5h 51m
BOS

Jun 3

ORD

as low as

$111

Washington, US (WAS) - Chicago, US (CHI)

United Airlines Logo
United Airlines

May 25

DCA
1h 16m
Direct

May 25

ORD

as low as

$115

Washington, US (WAS) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 25

DCA
1h 13m
Direct

May 25

ORD

as low as

$115

Washington, US (WAS) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

May 21

DCA
5h 42m
MSP

May 21

ORD

as low as

$124

Washington, US (WAS) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

May 19

DCA
4h 25m
ATL

May 19

ORD

as low as

$124

Washington, US (WAS) - Chicago, US (CHI)

United Airlines Logo
United Airlines

May 31

DCA
7h 6m
EWR

May 31

ORD

as low as

$134

Washington, US (WAS) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 20

DCA
2h 56m
CLE

May 20

ORD

as low as

$160

Washington, US (WAS) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 28

DCA
4h 21m
CLT

May 29

ORD

as low as

$160

Washington, US (WAS) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jun 11

DCA
5h 41m
LGA

Jun 11

ORD

as low as

$160

Washington, US (WAS) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 26

DCA
5h 23m
DAY

May 26

ORD

as low as

$175

Frequently Asked Questions

What is the typical flight duration from Reagan Washington National Airport to Chicago?
The typical flight from Reagan Washington National Airport to Chicago usually takes between 1.5 to 2.5 hours. This duration applies to direct flights and may vary with seasonal weather variations and air traffic. Travelers should plan for additional time for boarding and potential delays. It's advisable to check with the airline for the most up-to-date flight times before departure. This information is particularly useful for planning connections or ground transportation upon arrival, ensuring a smooth travel experience between these cities.
Are there any direct flights from Reagan Washington National Airport to Chicago?
Yes, there are direct flights available from Reagan Washington National Airport to Chicago. These nonstop flights typically range between 1.5 to 2.5 hours. This option is both time-efficient and convenient for travelers as it avoids the hassle of layovers. It's recommended to book early, as direct flights can be in high demand, particularly during peak travel seasons. This ensures a smoother transit from the originating city to your Chicago destination.
What are the best transportation options from Chicago airport to downtown or popular tourist attractions?
The best transportation options from Chicago's airports include a mix of shared shuttles, rideshare services, and public transit. Rideshares like Uber or Lyft generally cost between $20 to $40 and offer quick door-to-door service. The 'L' train system and Metra commuter trains provide economical options, with fares ranging from $2.50 to $5 per ride, though trips may take longer depending on your destination. Taxis are also available with rates typically running between $30 to $50. Each option provides varying levels of convenience and cost.
What are the must-see attractions in Chicago for travelers arriving from Reagan Washington National Airport?
Travelers arriving from Reagan Washington National Airport should consider visiting iconic landmarks such as Millennium Park, the Art Institute of Chicago, and Navy Pier. These spots offer rich cultural experiences and scenic views along Lake Michigan. Additional attractions include Willis Tower Skydeck and the Field Museum. While exploring, consider guided tours that provide historical context and insider tips. Each destination provides a memorable encounter with the vibrant art, architecture, and culinary scene unique to Chicago.
Which local dishes should travelers from Reagan Washington National Airport try when visiting Chicago?
Travelers should not miss trying Chicago’s famous deep-dish pizza, which offers a hearty, cheesy experience with a unique crust. Another must-try is the Italian beef sandwich, often served with giardiniera pickles for a spicy kick. Chicago-style hot dogs, prepared without ketchup but loaded with toppings, are also popular. For dessert, a slice of Eli's Cheesecake can be a delightful treat. These dishes represent the city’s diverse culinary heritage, offering flavors that resonate well with visitors from Reagan Washington National Airport.
What are the best family-friendly activities in Chicago for visitors from Reagan Washington National Airport?
Families arriving from Reagan Washington National Airport have a variety of engaging activities in Chicago. The Shedd Aquarium and the Field Museum provide educational and interactive exhibits suitable for children. The Lincoln Park Zoo offers a cost-free opportunity to see animals and enjoy outdoor activities. Millennium Park hosts seasonal events and outdoor concerts that appeal to all ages. Recreational boat tours along Lake Michigan deliver scenic views and a fun experience. These attractions provide both cultural enrichment and ample entertainment for every family member.
Are there any budget-friendly hotels in Chicago for travelers arriving from Reagan Washington National Airport?
Yes, there are budget-friendly hotels available in Chicago that offer convenient access to downtown attractions. Prices can range from $80 to $150 per night, depending on location and seasonal demand. These accommodations typically provide essential amenities such as free Wi-Fi, complimentary breakfast, and shuttle services to local attractions. It is wise to compare rates and book in advance, especially during peak tourism seasons, to secure the best deals. This approach ensures a comfortable stay without compromising on quality or location.
What are the top cultural experiences in Chicago that travelers from Reagan Washington National Airport should not miss?
Travelers should immerse themselves in Chicago's rich cultural landscape by visiting renowned institutions like the Art Institute of Chicago and the Chicago History Museum. Attending a performance at the Chicago Theatre or enjoying live jazz in local clubs further highlights the city’s vibrant arts scene. Neighborhoods such as Pilsen offer murals and local art installations that reflect the city’s diverse heritage. For a deeper dive, consider taking a guided architectural tour along the Chicago River to learn about its storied history and iconic skyscrapers.
What are the safety tips for travelers from Reagan Washington National Airport visiting Chicago?
For a safe visit, travelers should exercise common-sense precautions. Always be aware of your surroundings and secure your belongings, especially in crowded tourist areas. Use trusted transportation services like licensed taxis or reputable rideshares. Avoid isolated areas at night and remain informed about local news updates. When using public transit, watch for personal items and keep a copy of important documents. Additionally, research the neighborhoods you plan to visit in Chicago for any travel advisories. Staying informed and cautious helps ensure a secure and enjoyable trip.
Is there a specific time of year when Chicago is best visited by travelers from Reagan Washington National Airport?
Yes, the best times to visit Chicago are during the spring (April to June) and fall (September to October) seasons. During these periods, the weather is typically mild and comfortable, making outdoor activities more enjoyable. Additionally, these seasons offer fewer crowds and often lower travel costs compared to the busy summer months. Events like festivals and cultural fairs add extra charm to a visit. Travelers from Reagan Washington National Airport will appreciate the pleasant climate and vibrant atmosphere that enhance the overall travel experience.
What are the best places to shop for souvenirs in Chicago for travelers from Reagan Washington National Airport?
When shopping for souvenirs, travelers should explore areas such as the Magnificent Mile and local markets like the Chicago French Market. Boutiques in neighborhoods like Wicker Park offer unique, locally crafted items. Souvenir shops near Millennium Park and Navy Pier also provide a wide range of memorabilia, from Chicago-themed apparel to artisanal goods. It is advisable to compare prices and quality across different locations. This strategy helps in finding authentic keepsakes that capture the essence of Chicago, ensuring a memorable memento of your trip.
What unique airport amenities can travelers expect at Chicago for their arrival from Reagan Washington National Airport?
Travelers arriving in Chicago can enjoy various modern airport amenities designed to enhance the travel experience. Many terminals feature free Wi-Fi, comfortable lounges, and a diverse range of dining options. Automated check-in kiosks and enhanced security lines expedite processing times. Some terminals even offer retail shops selling local souvenirs and duty-free items. Additionally, dedicated charging stations and family-friendly zones are becoming more common. These features are tailored to make the transition from Reagan Washington National Airport to Chicago as seamless and enjoyable as possible.
Are there any seasonal events in Chicago that travelers from Reagan Washington National Airport should not miss?
Yes, Chicago hosts a variety of seasonal events worth planning around. In the summer, events like the Chicago Air and Water Show and Taste of Chicago offer vibrant cultural displays. In winter, the Christkindlmarket and festive light displays across downtown create a magical atmosphere. Spring often brings outdoor festivals and art fairs. These events showcase the city’s cultural diversity and vibrant social scene. Scheduling your visit during these peak times can provide immersive local experiences and an opportunity to engage with the community through unique festivities.
What are the customs requirements for travelers flying from Reagan Washington National Airport to Chicago?
Since both Reagan Washington National Airport and Chicago are within the United States, there are no international customs requirements. Travelers simply need valid government-issued photo identification such as a driver’s license or passport for security checks. However, it is important to ensure that all carry-on items comply with Transportation Security Administration (TSA) guidelines. Staying updated with the latest TSA regulations on liquids, electronics, and prohibited items is advisable to avoid delays. This streamlined process ensures that domestic flights remain hassle-free.
What are the best seating options for families traveling from Reagan Washington National Airport to Chicago?
Airlines often accommodate family groups by offering seating arrangements that cater to varying needs. Booking seats in advance can secure adjacent seating or bulkhead rows, which provide extra legroom and easier access to onboard facilities. Special requests such as child seating and bassinet options are frequently available during the booking process. It is advisable to contact the airline directly prior to travel for specific configurations. These measures help create a more comfortable and organized travel experience, ensuring that family members have convenient and safe seating throughout the journey.