
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $209 (Kiwi.com) |
One-way from | $99 (Delta) |
Popular in | April |
Cheapest in | September |
Average price | $293 |
Good round-trip deal | $309 or less |
Good one-way deal | $176 or less |
Fly from
Fly to
Route
Depart
Return
BaltimoreChicago
BWI - MDW
BWIMDW
Baltimore/Washington
Sat 6/6
9:25 pm-10:25 pm
Nonstop2h 00m
Chicago Midway
Wed 6/10
7:35 pm-10:25 pm
Nonstop1h 50m
BaltimoreChicago
BWI - ORD
BWIORD
Baltimore/Washington
Wed 5/27
8:25 am-9:39 am
Nonstop2h 14m
Chicago O'Hare Intl
Thu 6/4
6:20 pm-9:26 pm
Nonstop2h 06m
Washington, D.C.Chicago
IAD - MDW
IADMDW
Washington, D.C. Dulles Intl
Mon 6/1
6:00 am-8:43 am
1 stop3h 43m
Chicago Midway
Wed 6/3
6:36 pm-10:56 pm
1 stop3h 20m
Washington, D.C.Chicago
DCA - MDW
DCAMDW
Washington, D.C. Reagan-National
Sat 6/6
6:05 am-8:43 am
1 stop3h 38m
Chicago Midway
Wed 6/10
1:26 pm-6:59 pm
1 stop4h 33m
Washington, D.C.Chicago
DCA - MDW
DCAMDW
Washington, D.C. Reagan-National
Sat 6/6
6:10 am-7:10 am
Nonstop2h 00m
Chicago Midway
Wed 6/10
5:05 pm-7:55 pm
Nonstop1h 50m
Washington, D.C.Chicago
DCA - MDW
DCAMDW
Washington, D.C. Reagan-National
Sat 6/6
6:05 am-8:43 am
1 stop3h 38m
Chicago Midway
Tue 6/9
9:17 am-4:34 pm
1 stop6h 17m
Washington, D.C.Chicago
DCA - ORD
DCAORD
Washington, D.C. Reagan-National
Thu 6/11
7:15 am-8:29 am
Nonstop2h 14m
Chicago O'Hare Intl
Tue 6/16
6:00 am-8:54 am
Nonstop1h 54m
Washington, D.C.Chicago
IAD - ORD
IADORD
Washington, D.C. Dulles Intl
Tue 6/9
8:15 am-9:36 am
Nonstop2h 21m
Chicago O'Hare Intl
Sat 6/13
3:53 pm-7:02 pm
Nonstop2h 09m
Washington, D.C.Chicago
DCA - MDW
DCAMDW
Washington, D.C. Reagan-National
Wed 7/15
9:30 pm-10:30 pm
Nonstop2h 00m
Chicago Midway
Sat 7/18
11:05 am-1:50 pm
Nonstop1h 45m
BaltimoreChicago
BWI - ORD
BWIORD
Baltimore/Washington
Wed 6/17
7:05 pm-8:29 pm
Nonstop2h 24m
Chicago O'Hare Intl
Thu 6/18
6:20 am-9:17 am
Nonstop1h 57m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars |
To ensure you get the cheapest price possible for a flight from Washington, D.C. to Chicago, you should look to book at least 83 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Currently, August is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of $211). Flying from Washington, D.C. to Chicago in February is currently the most expensive (average of $420). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Unlike in the morning, when flights are generally more expensive, you can save up to 16% on flights from Washington, D.C. to Chicago by exploring options for tickets in the evening.
Travelers seeking maximum savings on their Washington, D.C. to Chicago flight should consider departing on Monday afternoons when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from WAS to CHI are scheduled on a Thursday (98 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (47 on average).
Boarding
Comfort
Overall
Crew
Entertainment
Food
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Comfort
Overall
Crew
Entertainment
Food
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Comfort
Overall
Crew
Entertainment
Food
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Comfort
Overall
Crew
Entertainment
Food
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Comfort
Overall
Crew
Entertainment
Food
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Comfort
Overall
Crew
Entertainment
Food
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$43 | Average$118 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$57 | Average$171 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$134 | Average$303 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$149 | Average$342 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$152 | Average$348 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$158 | Average$317 | FlexibilityNo cancel fee | On-time71% |