Cheap flights from Washington, D.C. to Chicago from $89
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Washington, D.C. to Chicago departing on 11/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Fly from
Fly to
Route
Depart
Return
BaltimoreChicago
BWI Baltimore/Washington - ORD Chicago O'Hare Intl
BWIORD
Baltimore/Washington
Mon 10/26
9:58 am-11:21 am
Nonstop2h 23m
Chicago O'Hare Intl
Thu 10/29
6:00 am-8:57 am
Nonstop1h 57m
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Sat 11/14
10:12 am-5:47 pm
1 stop8h 35m
Chicago Midway
Thu 11/19
6:08 am-4:44 pm
1 stop9h 36m
BaltimoreChicago
BWI Baltimore/Washington - ORD Chicago O'Hare Intl
BWIORD
Baltimore/Washington
Wed 11/4
6:10 am-7:31 am
Nonstop2h 21m
Chicago O'Hare Intl
Mon 11/9
11:00 am-2:06 pm
Nonstop2h 06m
BaltimoreChicago
BWI Baltimore/Washington - ORD Chicago O'Hare Intl
BWIORD
Baltimore/Washington
Wed 11/4
12:34 pm-1:54 pm
Nonstop2h 20m
Chicago O'Hare Intl
Sat 11/7
11:00 am-2:06 pm
Nonstop2h 06m
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Tue 1/5
5:50 pm-6:55 pm
Nonstop2h 05m
Chicago Midway
Sat 1/9
4:55 pm-7:45 pm
Nonstop1h 50m
BaltimoreChicago
BWI Baltimore/Washington - MDW Chicago Midway
BWIMDW
Baltimore/Washington
Wed 11/25
10:05 pm-11:15 pm
Nonstop2h 10m
Chicago Midway
Wed 12/2
8:50 am-11:40 am
Nonstop1h 50m
BaltimoreChicago
BWI Baltimore/Washington - ORD Chicago O'Hare Intl
BWIORD
Baltimore/Washington
Tue 1/5
11:00 am-12:31 pm
Nonstop2h 31m
Chicago O'Hare Intl
Sat 1/9
8:01 am-11:14 am
Nonstop2h 13m
BaltimoreChicago
BWI Baltimore/Washington - ORD Chicago O'Hare Intl
BWIORD
Baltimore/Washington
Tue 11/17
7:18 am-8:50 am
Nonstop2h 32m
Chicago O'Hare Intl
Tue 11/17
9:00 pm-11:55 pm
Nonstop1h 55m
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl
DCAORD
Washington, D.C. Reagan-National
Sat 11/7
6:00 pm-12:21 am
1 stop7h 21m
Chicago O'Hare Intl
Mon 11/9
7:00 am-9:59 am
1 stop25h 59m
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - ORD Chicago O'Hare Intl
DCAORD
Washington, D.C. Reagan-National
Sat 10/31
6:00 pm-12:21 am
1 stop7h 21m
Chicago O'Hare Intl
Mon 11/2
2:50 pm-9:59 am
1 stop18h 09m
See travel insights to Chicago from
How to get the cheapest flight ticket from Washington, D.C. to Chicago
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Washington, D.C. and Chicago?
Prices are currently low for flights on this route.
Typical prices usually range from $223 to $395.The lowest price recently found on this route was $175.
What is the cheapest month to fly to Chicago?
The month of January is, on average, the cheapest month to fly to Chicago from Washington, D.C., with most prices found around $293. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from Washington, D.C. to Chicago during February average around $301.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $410. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Washington, D.C. to Chicago for around $532.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Washington, D.C. to Chicago during this time can be as low as $426. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $462.
What is the cheapest Washington, D.C. to Chicago flight route?
Fly from Baltimore/Washington to Chicago O'Hare Intl for the best Washington, D.C. - Chicago flight prices
How far in advance should I book a flight from Washington, D.C. to Chicago?
You are more likely to see cheaper flights to Chicago from Washington, D.C. when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $410 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Washington, D.C. for as low as $302 on momondo.
What cabin class options are available on Washington, D.C. to Chicago flights?
There are 4 cabin classes available to choose from on Washington, D.C. to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Washington, D.C. to Chicago flights?
No. A direct flight is the cheapest option for a flight between Washington, D.C. to Chicago.
How have Washington, D.C. to Chicago flight prices changed over time?
As of October 2026, prices for Washington, D.C. to Chicago flights are approximately 6% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from Washington, D.C. to Chicago?
Southwest, United Airlines, and Frontier are the most popular carriers operating from Washington, D.C. to Chicago
What airlines fly to Chicago?
United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Washington, D.C. according to our data. United Airlines is the first choice among our users, with 56% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
Which airport is the most popular layover for flights between Washington, D.C. and Chicago?
Atlanta (ATL) was the most common stop: 69% of momondo users choosing 1-stop flights on this route connected there.
Which layover airport offers the lowest fares from Washington, D.C. to Chicago?
Flights via New York (JFK) offer the lowest average round-trip price of $152.
Which layover airport has the shortest travel time from Washington, D.C. to Chicago?
Flights connecting via New York (JFK) have the shortest average one-way travel time: 4h 57m.
Which layover airport has the shortest connection time from Washington, D.C. to Chicago?
New York (JFK) has the shortest average layover time for this route: 2h 01m.
How many flights depart from Washington, D.C. to Chicago on average per day?
As of October 2026, there are 86 flights per day flying from Washington, D.C. to Chicago. The most common time of day flights depart is 5:00PM, with 47% of flights taking off at noon.
How many flights depart from Washington, D.C. to Chicago on average per week?
As of October 2026, 603 flights take off from Washington, D.C. and land in Chicago each week. The most common flight departure day for this route is Mon, with 22% of weekly flights taking off on this day.
When to book flights from Washington, D.C. to Chicago
Cheap Washington, D.C. to Chicago (WAS to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Washington, D.C. to Chicago
Frequently asked questions about flying from Washington, D.C. to Chicago
How far is Washington, D.C. to Chicago by plane?
The straight-line distance from Washington, D.C. to Chicago is 593.1 mi. 2h 00m is a normal flight duration for this route.
When did momondo last update prices for flights from Washington, D.C. to Chicago?
Prices for flights from Washington, D.C. to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Washington, D.C. to Chicago?
There are 5 operators available for flights from Washington, D.C. to Chicago as of October 2026.
How old do you have to be to fly from Washington, D.C. to Chicago?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Washington, D.C. to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Washington, D.C. to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Washington, D.C. to Chicago is Boeing 737 MAX 8, representing 14.32% of all bookings. The subsequent popular models are Boeing 737-800 at 11.48%, Airbus A319 at 10.37%, and Airbus A321neo at 9.82%.
What is the most popular airline from Washington, D.C. to Chicago?
momondo data reveals that the most frequently booked airline on the route from Washington, D.C. to Chicago is United Airlines, representing 33% of all bookings. The subsequent popular airlines are Southwest at 27%, American Airlines at 21%, and Frontier at 18%.
Best airlines flying from Washington, D.C. to Chicago
Compare and see reviews for airlines that fly from Washington, D.C. to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $29 | Free Cancellation | Rating 5.5 2,550 reviews | |||
| PriceFrom $149 | Free Cancellation | Rating 7.8 8,634 reviews | |||
| PriceFrom $177 | Free Cancellation | Rating 7.4 10,288 reviews | |||
| PriceFrom $187 | Free Cancellation | Rating 7.0 12,128 reviews | |||
| PriceFrom $188 | Free Cancellation | Rating 7.9 4,215 reviews |
Southwest Flights From Washington, D.C. to Chicago
Southwest flies from Washington, D.C. to Chicago around 18 times per week, with 4,215 momondo users rating the airline 7.9/10. The cheapest Southwest deal from Washington, D.C. to Chicago in the last 72 hours was $188 (round-trip), much lower than the average airfare cost of $374 for Southwest flights on this route.
United Airlines Flights From Washington, D.C. to Chicago
The best United Airlines deal for Washington, D.C. to Chicago flight tickets found on momondo in the last 72 hours was $177, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $382 round-trip. United Airlines operates 92 flights out of Washington, D.C. into Chicago in an average week, so prices vary by time and availability. 10,288 United Airlines reviews by users on momondo have scored the airline at 7.4/10.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Washington, D.C. to Chicago?
It is quick and easy to find Washington, D.C. to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.
Can I find flights from Washington, D.C. to Chicago with flexible booking policies on momondo?
Flights from Washington, D.C. to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Washington, D.C. to Chicago?
Once you have performed a search for Washington, D.C. to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.
I’m not ready to book a flight from Washington, D.C. to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from Washington, D.C. are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.