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Flight Deals from Washington to Chicago from $94

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Stops

  • Nonstop
    from $229
  • Up to 1 stop
    $189
  • Up to 2 stops
    $318

Airlines

  • American Airlines
    $229
  • Delta Air Lines
    $197
  • Frontier Airlines
    $189
  • JetBlue
    $219
  • Southwest Airlines
    $295
  • United Airlines
    $229

Cabin Class

  • Economy
    $189

Departure Airports

  • Reagan Washington National Airport
    $198
  • Washington Dulles Airport
    $189

Arrival Airports

  • Chicago Midway Airport
    $197
  • Chicago O Hare Airport
    $189

Layover Airports

  • Charlotte Douglas International Airport
    $275
  • Denver International Airport
    $219
  • Detroit Metropolitan Airport
    $197
  • General Edward Lawrence Logan International Airport
    $219
  • Hartsfield Jackson Atlanta International Airport
    $197
  • John Glenn Columbus International Airport
    $275
  • Kansas City International Airport
    $318
  • Minneapolis-St Paul International/Wold-Chamberlain Airport
    $223
  • New York John F Kennedy Airport
    $219
  • New York LaGuardia Airport
    $270
  • Newark Liberty Airport
    $269
  • Orlando International Airport
    $189
  • Pittsburgh International Airport
    $299
  • Raleigh Durham International Airport
    $279
  • St Louis Lambert International Airport
    $318
  • Tampa International Airport
    $189

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On average save $240 per traveler
Frontier Airlines Logo
Frontier Airlines

05/16/25

IAD
6h 6m
MCO

05/16/25

ORD
Frontier Airlines Logo
Frontier Airlines

05/18/25

ORD
16h 24m
TPA

05/19/25

IAD
$189
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/24/25

IAD
5h 36m
ATL

05/24/25

MDW
Delta Air Lines Logo
Delta Air Lines

05/31/25

MDW
4h 45m
DTW

05/31/25

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

05/25/25

IAD
3h 18m
DTW

05/25/25

ORD
Delta Air Lines Logo
Delta Air Lines

05/31/25

ORD
7h 6m
ATL

05/31/25

IAD
$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

IAD
8h 15m
ATL

05/19/25

MDW
Frontier Airlines Logo
Frontier Airlines

05/23/25

MDW
9h 23m
ATL

05/23/25

IAD
$199
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/15/25

IAD
6h 6m
MCO

05/15/25

ORD
Frontier Airlines Logo
Frontier Airlines

05/22/25

ORD
7h 54m
ATL

05/22/25

IAD
$209
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

05/21/25

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
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
Delta Air Lines Logo
Delta Air Lines

05/26/25

DCA
5h 42m
MSP

05/26/25

ORD
Delta Air Lines Logo
Delta Air Lines

05/30/25

ORD
4h 54m
DTW

05/30/25

DCA
$223
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/29/25

DCA
10h 52m
DEN

05/29/25

ORD
Frontier Airlines Logo
Frontier Airlines

06/05/25

ORD
6h 50m
ATL

06/05/25

DCA
$227
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
United Airlines Logo
United Airlines

05/24/25

IAD
1h 13m
Direct

05/24/25

ORD
United Airlines Logo
United Airlines

05/25/25

ORD
3h 3m
Direct

05/25/25

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

05/25/25

IAD
1h 13m
Direct

05/25/25

ORD
United Airlines Logo
United Airlines

05/29/25

ORD
3h 2m
Direct

05/29/25

IAD
$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
United Airlines Logo
United Airlines

06/05/25

IAD
4h 37m
EWR

06/05/25

ORD
United Airlines Logo
United Airlines

06/08/25

ORD
3h 3m
Direct

06/08/25

IAD
$269
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

06/12/25

IAD
4h 37m
EWR

06/12/25

ORD
United Airlines Logo
United Airlines

06/14/25

ORD
3h 3m
Direct

06/14/25

IAD
$269
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

05/24/25

IAD
4h 17m
CLT

05/24/25

ORD
American Airlines Logo
American Airlines

05/25/25

ORD
3h 1m
Direct

05/25/25

IAD
$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

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
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
Southwest Airlines Logo
Southwest Airlines

05/18/25

DCA
55m
Direct

05/18/25

MDW
Southwest Airlines Logo
Southwest Airlines

05/20/25

MDW
11h 20m
STL
MCI

05/20/25

DCA
$318
Free cancellation within 83 hours of booking

Top Deals on flights from Washington to Chicago

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

Frontier Airlines Logo
Frontier Airlines

May 15

IAD
6h 6m
MCO

May 15

ORD

as low as

$94

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

Delta Air Lines Logo
Delta Air Lines

May 24

IAD
5h 36m
ATL

May 24

MDW

as low as

$98

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

Delta Air Lines Logo
Delta Air Lines

May 25

IAD
3h 18m
DTW

May 25

ORD

as low as

$98

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

May 18

IAD
21h 39m
LAS

May 19

ORD

as low as

$100

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 24

DCA
1h 14m
Direct

May 24

ORD

as low as

$115

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

American Airlines Logo
American Airlines

May 25

DCA
1h 27m
Direct

May 25

ORD

as low as

$115

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)

 Logo

May 22

IAD
4h 32m
MSP

May 22

ORD

as low as

$138

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

American Airlines Logo
American Airlines

Jun 3

DCA
3h
IND

Jun 3

ORD

as low as

$160

Frequently Asked Questions

What is the typical flight duration from Washington to Chicago?
Typically, a flight from Washington to Chicago takes between 1.5 to 2 hours of actual air time. However, when you include taxiing, boarding procedures, and potential minor delays, the overall journey can last between 2 to 2.5 hours. It’s wise to arrive at the airport at least 90 minutes to two hours beforehand for domestic flights. Keep in mind that actual flight times may vary slightly depending on weather conditions and air traffic. Checking your airline’s schedule for updated timing is a practical tip.
Are there any direct flights from Washington to Chicago?
Yes, there are multiple direct flights offered between Washington and Chicago daily by several carriers. Direct flights typically cut down travel time by eliminating layovers, ensuring a smoother journey. Prices vary and can range from $100 to $300 depending on the season and booking time. It is advisable to book early to secure the best fare and to check both major airports in Washington and Chicago to compare options for departure and arrival times.
What are the best transportation options from Chicago airport to downtown?
When arriving at Chicago’s airport, travelers can choose among several transportation options. The CTA ‘L’ train offers a convenient ride to downtown with fares usually ranging from $5 to $7. Taxis and rideshares like Uber or Lyft provide door-to-door service with costs typically between $30 and $50, depending on traffic and time of day. Shuttle services and car rentals are also available. Evaluate cost, luggage requirements, and time of travel when selecting the best option for a comfortable transfer.
What are the must-see attractions in Chicago for travelers arriving from Washington?
Chicago boasts a range of attractions that make it a unique destination. Visitors should consider exploring Millennium Park, Navy Pier, and the Art Institute of Chicago for a taste of local culture and art. Architectural boat tours allow for a different perspective of the city’s skyline, while a visit to the Willis Tower Skydeck offers breathtaking views. Additionally, exploring neighborhoods with distinctive culinary and historical experiences can add extra value to the trip. These attractions have varying entry fees and tour costs, so it is wise to plan your itinerary in advance.
Which local dishes should travelers from Washington try when visiting Chicago?
Travelers visiting Chicago should not miss sampling the city’s iconic local dishes. Deep-dish pizza is a must-try, offering a hearty, cheesy experience with a crust that’s a meal in itself. Chicago-style hot dogs and Italian beef sandwiches, often served with giardiniera, are also popular. Prices for a meal generally range between $10 to $25. Dining at local, well-loved establishments can provide an authentic taste of the city’s culinary heritage, ensuring a satisfying gastronomic adventure during your visit.
Are there any family-friendly activities in Chicago for visitors from Washington?
Yes, Chicago offers a wide variety of family-friendly activities suitable for different ages. Families can enjoy interactive experiences at the Shedd Aquarium and the Field Museum, or explore the Lincoln Park Zoo, which offers free admission. Millennium Park also hosts seasonal outdoor events and playgrounds geared towards children. Additionally, various museums and recreational parks provide engaging activities for a day out. Planning ahead for ticket purchases and seasonal opera or cultural events can enhance the experience, ensuring an enjoyable and educational visit for all family members.
What are the best budget-friendly hotels in Chicago for travelers from Washington?
Several budget-friendly hotels in Chicago offer comfort and accessibility without breaking the bank. Options in centrally located neighborhoods often offer rooms ranging from $100 to $200 per night, especially during off-peak seasons. Chain hotels and local boutique accommodations near public transportation hubs ensure convenient access to the city’s top attractions. Comparisons on travel websites and booking systems can help identify deals, and considering hotels slightly outside the immediate downtown area may yield even better rates. Always check recent reviews to ensure quality and safety during your stay.
What cultural events or festivals are happening in Chicago that travelers from Washington should know about?
Chicago hosts a vibrant array of cultural events and festivals throughout the year. Travelers can experience the Taste of Chicago, art festivals, and music events that celebrate diverse communities, along with seasonal exhibitions at local theaters and museums. The Chicago Air and Water Show, typically held in the summer, offers an exciting spectacle over the lakefront. Since these events have variable dates and entry fees, it is a good idea to check the local events calendar and websites for updated schedules, ensuring you experience the city’s rich cultural tapestry during your visit.
What are the top outdoor activities in Chicago for visitors from Washington?
Outdoor enthusiasts will find plenty to do in Chicago. Activities include biking along the lakeside trail, taking scenic walks in Grant Park, or enjoying a leisurely boat ride on the Chicago River. Visitors can also explore local parks, attend outdoor yoga sessions, or kayak on nearby waterways during warmer months. Costs for rentals or tours can range from $15 to $50, depending on the duration and type of activity. These options offer a refreshing way to discover the urban outdoors while experiencing the city’s dynamic natural and architectural beauty.
What are the customs requirements for travelers flying from Washington to Chicago?
Since both Washington and Chicago are within the United States, there are no customs requirements for travelers on this route. Domestic flights operate under TSA security guidelines, where travelers should have a valid form of identification like a driver’s license or passport. This makes the process straightforward compared to international travel. However, it’s still important to comply with all TSA regulations regarding liquids and prohibited items. Keeping updated with any potential changes in airport security policies can help ensure a hassle-free journey.
Is there a specific time of year when Chicago is best visited by travelers from Washington?
Yes, many find that late spring to early fall, especially between May and September, offers the most pleasant weather and vibrant atmosphere. During these months, the city hosts various outdoor festivals, events, and concerts, which enhance the visitor experience. Although peak tourist periods may see higher prices and crowds, planning a visit during shoulder seasons like May or September can provide a balanced combination of comfortable weather, lower accommodation costs, and fewer tourists. This timing allows for an immersive, enjoyable exploration of the city.
What are the best shopping districts in Chicago for travelers from Washington?
Chicago is renowned for its diverse shopping communities. The Magnificent Mile is a popular destination featuring high-end retail stores, designer brands, and unique boutiques. Additionally, State Street offers a blend of mainstream shops and local retailers perfect for various budgets. Neighborhoods like Wicker Park and Lincoln Park provide an eclectic shopping experience with independent stores and vintage finds. Prices vary widely, so it’s a good idea to explore different areas based on your budget and shopping interests. Checking local guides and maps will help you create an enjoyable shopping itinerary.
Are there any special airport amenities in Chicago for travelers arriving from Washington?
Chicago’s airports offer several special amenities to enhance the travel experience. Many terminals feature comfortable lounges, free Wi-Fi, quality dining options, and retail shops for last-minute essentials. Some terminals also provide relaxation zones, charging stations, and family areas, ensuring a more convenient transfer experience for various needs. The variety of services can cater to short layovers as well as long waits. It is advisable to explore the airport maps or ask at information desks to locate these amenities, ensuring a more comfortable and streamlined arrival experience.
What health precautions should travelers from Washington take when visiting Chicago?
Travelers should consider standard health precautions when visiting Chicago. It is wise to stay updated on seasonal vaccinations, such as the flu shot, and carry any necessary personal medications. Given the urban setting, practicing common-sense hygiene—like frequent hand washing and using hand sanitizers—can help prevent illnesses. Additionally, monitor local weather forecasts as Chicago can experience extreme weather variations. Checking for any local health advisories or COVID-related updates before your trip is also recommended. Being prepared with a basic health kit will ensure a safer, more relaxed visit.
What are the best seating options for families traveling from Washington to Chicago?
Airlines typically offer several seating options tailored for family comfort. Many carriers provide bulkhead seats, which offer extra legroom and a bit more space for children, along with the option to secure seats together as a family. Reserving seats in advance, or checking in early, increases the likelihood of obtaining seating that best fits family needs. Some families opt for window and aisle combinations to help keep children engaged and provide extra space for strollers if needed. It is advisable to contact your airline directly to inquire about available seating configurations and any family-oriented services.