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Cheap Flights from Washington D.C. to Chicago

Explore the cheapest flights from Washington D.C. to Chicago in the next three months. Based on Trip.com's data from the latest 7 days, one-way direct flights start at S$ 113, and round-trip direct tickets start at S$ 219.

      • Cheapest nonstop
        DCA 15:52
        2h 33m
        Direct
        ORD 17:25
        Washington D.C. - Chicago | Thu, Jun 25 | American Airlines
        MDW 05:40
        1h 45m
        Direct
        DCA 08:25
        Chicago - Washington D.C. | Thu, Jul 2 |
        S$ 219 S$ 300
        27% off
        27% off
        S$ 300 S$ 219
      • IAD 17:26
        5h 36m
        1 stop
        MDW 22:02
        Washington D.C. - Chicago | Wed, May 13 | Frontier Airlines
        ORD 13:59
        8h 10m
        1 stop
        IAD 23:09
        Chicago - Washington D.C. | Sat, May 16 | Frontier Airlines
        S$ 181 S$ 300
        40% off
        40% off
        S$ 300 S$ 181
      • IAD 17:26
        5h 36m
        1 stop
        MDW 22:02
        Washington D.C. - Chicago | Sun, May 17 | Frontier Airlines
        ORD 06:55
        8h 26m
        1 stop
        IAD 16:21
        Chicago - Washington D.C. | Wed, May 20 | Frontier Airlines
        S$ 182 S$ 300
        39% off
        39% off
        S$ 300 S$ 182
      • IAD 17:07
        7h 6m
        1 stop
        ORD 23:13
        Washington D.C. - Chicago | Thu, May 14 | Frontier Airlines
        MDW 06:00
        10h 27m
        1 stop
        IAD 17:27
        Chicago - Washington D.C. | Thu, May 21 | Frontier Airlines
        S$ 186
        38% off
        S$ 300 S$ 186
      • DCA 06:05
        3h 38m
        1 stop
        MDW 08:43
        Washington D.C. - Chicago | Mon, May 25 | Delta Air Lines
        ORD 17:08
        5h 36m
        1 stop
        DCA 23:44
        Chicago - Washington D.C. | Sat, May 30 | Delta Air Lines
        S$ 195
        35% off
        S$ 300 S$ 195
      • DCA 06:05
        3h 40m
        1 stop
        ORD 08:45
        Washington D.C. - Chicago | Thu, Jun 4 | Delta Air Lines
        ORD 12:53
        5h 52m
        1 stop
        DCA 19:45
        Chicago - Washington D.C. | Fri, Jun 5 | Delta Air Lines
        S$ 195
        35% off
        S$ 300 S$ 195
      • IAD 19:27
        28h 46m
        1 stop
        ORD 23:13
        Washington D.C. - Chicago | Tue, May 12 | Frontier Airlines
        ORD 17:30
        23h 22m
        1 stop
        IAD 17:52
        Chicago - Washington D.C. | Tue, May 19 | Frontier Airlines
        S$ 198
        34% off
        S$ 300 S$ 198
      • IAD 06:00
        3h 43m
        1 stop
        MDW 08:43
        Washington D.C. - Chicago | Sun, May 31 | Delta Air Lines
        ORD 07:05
        4h 34m
        1 stop
        DCA 12:39
        Chicago - Washington D.C. | Sun, Jun 7 | Delta Air Lines
        S$ 202
        33% off
        S$ 300 S$ 202
      • DCA 06:05
        3h 38m
        1 stop
        MDW 08:43
        Washington D.C. - Chicago | Tue, Jun 2 | Delta Air Lines
        ORD 14:59
        4h 46m
        1 stop
        DCA 20:45
        Chicago - Washington D.C. | Thu, Jun 4 | Delta Air Lines
        S$ 202
        33% off
        S$ 300 S$ 202
      • IAD 06:00
        3h 43m
        1 stop
        MDW 08:43
        Washington D.C. - Chicago | Wed, May 27 | Delta Air Lines
        ORD 17:19
        4h 37m
        1 stop
        IAD 22:56
        Chicago - Washington D.C. | Sun, May 31 | Delta Air Lines
        S$ 203
        32% off
        S$ 300 S$ 203
      • DCA 18:30
        4h 47m
        1 stop
        MDW 22:17
        Washington D.C. - Chicago | Tue, Jun 9 | Delta Air Lines
        ORD 17:22
        4h 37m
        1 stop
        DCA 22:59
        Chicago - Washington D.C. | Thu, Jun 11 | Delta Air Lines
        S$ 204
        32% off
        S$ 300 S$ 204
      • WAS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Washington D.C. - Chicago | Wed, May 13 | Normal Airline
        CHI 15:00
        6h
        Direct
        WAS 16:00
        Chicago - Washington D.C. | Fri, May 15 | Normal Airline
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      • Cheapest nonstop
        DCA 22:10
        2h 20m
        Direct
        ORD 23:30
        Washington D.C. - Chicago | Thu, Jun 18 | American Airlines
        S$ 113 S$ 161
        30% off
        30% off
        S$ 161 S$ 113
      • DCA 20:06
        2h 31m
        Direct
        ORD 21:37
        Washington D.C. - Chicago | Wed, Jun 24 | American Airlines
        S$ 117 S$ 161
        27% off
        27% off
        S$ 161 S$ 117
      • IAD 17:26
        5h 36m
        1 stop
        MDW 22:02
        Washington D.C. - Chicago | Sun, May 17 | Frontier Airlines
        S$ 88 S$ 161
        45% off
        45% off
        S$ 161 S$ 88
      • IAD 17:26
        5h 36m
        1 stop
        MDW 22:02
        Washington D.C. - Chicago | Wed, May 20 | Frontier Airlines
        S$ 111
        31% off
        S$ 161 S$ 111
      • IAD 06:00
        5h 9m
        1 stop
        MDW 10:09
        Washington D.C. - Chicago | Thu, Jun 18 | Delta Air Lines
        S$ 112
        30% off
        S$ 161 S$ 112
      • IAD 17:26
        5h 36m
        1 stop
        MDW 22:02
        Washington D.C. - Chicago | Wed, May 13 | Frontier Airlines
        S$ 116
        28% off
        S$ 161 S$ 116
      • IAD 11:12
        9h 39m
        1 stop
        ORD 19:51
        Washington D.C. - Chicago | Tue, May 19 | Frontier Airlines
        S$ 116
        28% off
        S$ 161 S$ 116
      • IAD 06:14
        7h 55m
        1 stop
        MDW 13:09
        Washington D.C. - Chicago | Thu, Jun 11 | Delta Air Lines
        S$ 117
        27% off
        S$ 161 S$ 117
      • WAS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Washington D.C. - Chicago | Wed, May 13 | Normal Airline
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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Trip.com Price Insights on Flights from Washington D.C. to Chicago.

What is the cheapest month for one-way flights from to Chicago?

The average price of one-way flights from to Chicago purchased by Trip.com users by month over the past 12 months.

Based on Trip.com’s data, the cheapest month for flights from to Chicago is August, with an average price of S$ 206, and the most expensive month is July, with an average price of up to S$ 330.

S$ 330
S$ 268
S$ 206
S$ 144
    Cheapest
  • S$ 278
    May
  • S$ 302
    Jun
  • S$ 330
    Jul
  • S$ 206
    Aug
  • S$ 249
    Sep
  • S$ 327
    Oct
  • S$ 302
    Nov
  • S$ 270
    Dec
  • S$ 254
    Jan
  • S$ 315
    Feb
  • S$ 282
    Mar
  • S$ 305
    Apr

What is the cheapest day to fly from Washington D.C. to Chicago during Hari Raya Haji?

Based on Trip.com's data over the past 3 days, these are the lowest one-way airfares from Washington D.C. to Chicago during Hari Raya Haji.

Hari Raya Haji is scheduled on May 27. The flights from Washington D.C. to Chicago are cheapest on May 29, with the lowest fare of S$ 149.

S$ 197
S$ 173
S$ 149
S$ 125
    Cheapest
  • S$ 197
    23
    May
  • S$ 163
    24
  • S$ 163
    25
  • S$ 186
    26
  • S$ 160
    27
  • S$ 161
    28
  • S$ 149
    29

Frequently Asked Questions

  • Which airlines offer the cheapest flights from Washington D.C. (WAS) to Chicago (CHI)?

    Based on Trip.com data, Frontier Airlines offers one-way fares as low as S$ 88 on Cheapest nonstop routes (e.g. IAD to MDW on Sun, May 17), while Frontier Airlines offers Cheapest nonstop round-trips from S$ 181 departing on Wed, May 13 and returning on Sat, May 16.
  • At the moment, you can catch a direct flight from Washington D.C. to Chicago with the following airlines, including: United Airlines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.
  • It takes about 2 hours 13 minutes to fly from Washington D.C. (WAS) to Chicago (CHI).
  • By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Washington D.C. to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.
  • Based on Trip.com data in the past 4 weeks, there is 198 flight per week flying from Washington D.C. to Chicago. You can check the weekly schedule for popular airlines on this route below: United Airlines: S/M/T/W/T/F/S -- UA3572 (08:51)
  • To find best deals on flights from Washington D.C. to Chicago, you can use various tools on Trip.com:
    · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Sun, May 17, with one-way flights priced at just S$ 88.
    · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is American Airlines.
    · Set up price alerts to easily monitor ticket prices without having to check every day.
    · Check Trip.com flight deals and promo codes frequently.
    · Avoid peak season unless you book very early. It seems the peak season for Chicago travel is around July.
    · Get exclusive promo codes for Trip.com app users.
  • The cheapest months to fly from Washington D.C. to Chicago is November, when demand for travel is lower.
  • After crunching the numbers on our May flight calendar, it's currently cheapest to fly from Washington D.C. to Chicago on May 19, 2026 with Frontier Airlines, with prices starting at S$ 62.
  • You can land at any one of the following hubs in Chicago, with Dulles International Airport to Chicago O'Hare International Airport (IAD-ORD) is by far the most common option on this route: Chicago O'Hare International Airport (ORD) Chicago Midway International Airport (MDW) Chicago Rockford International Airport (RFD).
  • The time difference between Chicago and Washington D.C. is 1h.
  • Tickets can only be changed or cancelled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.

Find Cheap Flights & Deals on Trip.com

Note: Prices shown on this page are the lowest estimated prices found in the last 24 hours and include all taxes and fees.

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Prices displayed on this page are all-inclusive (incl. taxes, fuel surcharges, Civil Aviation Development Fund, etc.), and all fees are shown before payment. Charges for checked baggage, meals, Wi-Fi, and other optional services may also appear in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page have been updated within the last 24 hours, and with many routes refreshed in real time. The more popular the route, the more accurate the data.

Change & Cancellation Policy

Trip.com shows the change and cancellation rules for each ticket during the booking process, including all related fees and conditions. Please refer to the following scenarios:
Voluntary cancellation/change:
To request a change or cancellation, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and flight segment, and submit your request. Please note that additional charges may apply based on the airline’s fare rules.
Cancellation/change due to a flight schedule change:
If your flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For full details of change and cancellation policies, please refer to the customer support pages.