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Flights from Washington to Chicago (IAD to CHI)

Discover alternate routes & cheap one way flights from Washington to Chicago (IAD to CHI) within a departure date range.

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  • USD 109
    United Airlines
    10:10pm - 11:15pm
    Sat Jun 29th
    2h 5m
    Washington, D.C. (IAD) → Chicago (ORD)
    Direct

    Sat Jun 29th 2024 United Airlines · UA 1738 Depart at 10:10pm from Washington, D.C. (IAD) Fly for 2h 5m Arrive at 11:15pm in Chicago (ORD)

  • USD 109
    United Airlines
    10:10pm - 11:15pm
    Sun Jun 30th
    2h 5m
    Washington, D.C. (IAD) → Chicago (ORD)
    Direct

    Sun Jun 30th 2024 United Airlines · UA 1738 Depart at 10:10pm from Washington, D.C. (IAD) Fly for 2h 5m Arrive at 11:15pm in Chicago (ORD)

  • USD 109
    United Airlines
    8:15am - 9:25am
    Sun Jun 30th
    2h 10m
    Washington, D.C. (IAD) → Chicago (ORD)
    Direct

    Sun Jun 30th 2024 United Airlines · UA 2440 Depart at 8:15am from Washington, D.C. (IAD) Fly for 2h 10m Arrive at 9:25am in Chicago (ORD)

  • USD 109
    United Airlines
    6:30am - 7:40am
    Sun Jun 30th
    2h 10m
    Washington, D.C. (IAD) → Chicago (ORD)
    Direct

    Sun Jun 30th 2024 United Airlines · UA 2348 Depart at 6:30am from Washington, D.C. (IAD) Fly for 2h 10m Arrive at 7:40am in Chicago (ORD)

  • USD 142
    United Airlines
    5:33pm - 6:55pm
    Sat Jun 29th
    2h 22m
    Washington, D.C. (IAD) → Chicago (ORD)
    Direct

    Sat Jun 29th 2024 United Airlines · UA 2727 Depart at 5:33pm from Washington, D.C. (IAD) Fly for 2h 22m Arrive at 6:55pm in Chicago (ORD)

  • USD 148
    United Airlines
    6:30am - 7:40am
    Fri Jun 28th
    2h 10m
    Washington, D.C. (IAD) → Chicago (ORD)
    Direct

    Fri Jun 28th 2024 United Airlines · UA 2348 Depart at 6:30am from Washington, D.C. (IAD) Fly for 2h 10m Arrive at 7:40am in Chicago (ORD)

  • USD 154
    United Airlines
    5:33pm - 6:55pm
    Sun Jun 30th
    2h 22m
    Washington, D.C. (IAD) → Chicago (ORD)
    Direct

    Sun Jun 30th 2024 United Airlines · UA 2727 Depart at 5:33pm from Washington, D.C. (IAD) Fly for 2h 22m Arrive at 6:55pm in Chicago (ORD)

  • USD 156
    United Airlines
    6:30am - 7:40am
    Sat Jun 29th
    2h 10m
    Washington, D.C. (IAD) → Chicago (ORD)
    Direct

    Sat Jun 29th 2024 United Airlines · UA 2348 Depart at 6:30am from Washington, D.C. (IAD) Fly for 2h 10m Arrive at 7:40am in Chicago (ORD)

  • USD 159
    United Airlines
    10:10pm - 11:15pm
    Fri Jun 28th
    2h 5m
    Washington, D.C. (IAD) → Chicago (ORD)
    Direct

    Fri Jun 28th 2024 United Airlines · UA 1738 Depart at 10:10pm from Washington, D.C. (IAD) Fly for 2h 5m Arrive at 11:15pm in Chicago (ORD)

  • USD 159
    United Airlines
    1:10pm - 2:20pm
    Sun Jun 30th
    2h 10m
    Washington, D.C. (IAD) → Chicago (ORD)
    Direct

    Sun Jun 30th 2024 United Airlines · UA 2331 Depart at 1:10pm from Washington, D.C. (IAD) Fly for 2h 10m Arrive at 2:20pm in Chicago (ORD)

  • USD 159
    United Airlines
    8:15am - 9:25am
    Fri Jun 28th
    2h 10m
    Washington, D.C. (IAD) → Chicago (ORD)
    Direct

    Fri Jun 28th 2024 United Airlines · UA 2440 Depart at 8:15am from Washington, D.C. (IAD) Fly for 2h 10m Arrive at 9:25am in Chicago (ORD)

  • USD 173
    Sun Country Airlines
    7:00am - 6:36pm
    Sun Jun 30th
    12h 36m
    Washington, D.C. (IAD) → Chicago (ORD)
    1 Stop

    Sun Jun 30th 2024 Sun Country Airlines · SY 668 Depart at 7:00am from Washington, D.C. (IAD) Fly for 2h 46m Arrive at 8:46am in Minneapolis (MSP)

    Layover in Minneapolis for 8h 14m

    Sun Jun 30th 2024 Sun Country Airlines · SY 261 Depart at 5:00pm from Minneapolis (MSP) Fly for 1h 36m Arrive at 6:36pm in Chicago (ORD)

  • USD 187
    United Airlines
    8:15am - 9:25am
    Sat Jun 29th
    2h 10m
    Washington, D.C. (IAD) → Chicago (ORD)
    Direct

    Sat Jun 29th 2024 United Airlines · UA 2440 Depart at 8:15am from Washington, D.C. (IAD) Fly for 2h 10m Arrive at 9:25am in Chicago (ORD)

  • USD 189
    United Airlines
    1:10pm - 2:20pm
    Fri Jun 28th
    2h 10m
    Washington, D.C. (IAD) → Chicago (ORD)
    Direct

    Fri Jun 28th 2024 United Airlines · UA 2331 Depart at 1:10pm from Washington, D.C. (IAD) Fly for 2h 10m Arrive at 2:20pm in Chicago (ORD)

  • USD 193
    United Airlines
    6:00am - 9:52am
    Sun Jun 30th
    4h 52m
    Washington, D.C. (IAD) → Chicago (ORD)
    1 Stop

    Sun Jun 30th 2024 United Airlines · UA 2455 Depart at 6:00am from Washington, D.C. (IAD) Fly for 1h 17m Arrive at 7:17am in New York (EWR)

    Layover in New York for 1h 0m

    Sun Jun 30th 2024 United Airlines · UA 2100 Depart at 8:17am from New York (EWR) Fly for 2h 35m Arrive at 9:52am in Chicago (ORD)

  • USD 193
    United Airlines
    6:00am - 10:35am
    Sun Jun 30th
    5h 35m
    Washington, D.C. (IAD) → Chicago (ORD)
    1 Stop

    Sun Jun 30th 2024 United Airlines · UA 2455 Depart at 6:00am from Washington, D.C. (IAD) Fly for 1h 17m Arrive at 7:17am in New York (EWR)

    Layover in New York for 1h 43m

    Sun Jun 30th 2024 United Airlines · UA 2290 Depart at 9:00am from New York (EWR) Fly for 2h 35m Arrive at 10:35am in Chicago (ORD)

  • USD 199
    United Airlines
    1:05pm - 2:10pm
    Sat Jun 29th
    2h 5m
    Washington, D.C. (IAD) → Chicago (ORD)
    Direct

    Sat Jun 29th 2024 United Airlines · UA 2331 Depart at 1:05pm from Washington, D.C. (IAD) Fly for 2h 5m Arrive at 2:10pm in Chicago (ORD)

  • USD 202
    United Airlines
    10:15pm - 6:34am
    Fri Jun 28th
    9h 19m
    Washington, D.C. (IAD) → Chicago (ORD)
    1 Stop

    Fri Jun 28th 2024 United Airlines · UA 6130 Depart at 10:15pm from Washington, D.C. (IAD) Fly for 1h 43m Arrive at 11:58pm in Cincinnati (CVG)

    Layover in Cincinnati for 6h 2m

    Sat Jun 29th 2024 United Airlines · UA 3542 Depart at 6:00am from Cincinnati (CVG) Fly for 1h 34m Arrive at 6:34am in Chicago (ORD)

  • USD 202
    United Airlines
    10:15pm - 7:40am
    Fri Jun 28th
    10h 25m
    Washington, D.C. (IAD) → Chicago (ORD)
    1 Stop

    Fri Jun 28th 2024 United Airlines · UA 6130 Depart at 10:15pm from Washington, D.C. (IAD) Fly for 1h 43m Arrive at 11:58pm in Cincinnati (CVG)

    Layover in Cincinnati for 7h 12m

    Sat Jun 29th 2024 United Airlines · UA 2323 Depart at 7:10am from Cincinnati (CVG) Fly for 1h 30m Arrive at 7:40am in Chicago (ORD)

  • USD 203
    United Airlines
    6:00am - 10:40am
    Sat Jun 29th
    5h 40m
    Washington, D.C. (IAD) → Chicago (ORD)
    1 Stop

    Sat Jun 29th 2024 United Airlines · UA 2455 Depart at 6:00am from Washington, D.C. (IAD) Fly for 1h 17m Arrive at 7:17am in New York (EWR)

    Layover in New York for 1h 48m

    Sat Jun 29th 2024 United Airlines · UA 2290 Depart at 9:05am from New York (EWR) Fly for 2h 35m Arrive at 10:40am in Chicago (ORD)

  • USD 206
    Southern Airways ExpressUnited Airlines
    12:55pm - 6:35pm
    Sat Jun 29th
    6h 40m
    Washington, D.C. (IAD) → Chicago (ORD)
    2 Stops

    Sat Jun 29th 2024 Southern Airways Express · 9X 194 Depart at 12:55pm from Washington, D.C. (IAD) Fly for 1h 15m Arrive at 2:10pm in Morgantown (MGW)

    Layover in Morgantown for 0h 55m

    Sat Jun 29th 2024 Southern Airways Express · 9X 107 Depart at 3:05pm from Morgantown (MGW) Fly for 0h 40m Arrive at 3:45pm in Pittsburgh (PIT)

    Layover in Pittsburgh for 2h 10m

    Sat Jun 29th 2024 United Airlines · UA 602 Depart at 5:55pm from Pittsburgh (PIT) Fly for 1h 40m Arrive at 6:35pm in Chicago (ORD)

  • USD 206
    United Airlines
    10:12pm - 9:36am
    Sun Jun 30th
    12h 24m
    Washington, D.C. (IAD) → Chicago (ORD)
    1 Stop

    Sun Jun 30th 2024 United Airlines · UA 3540 Depart at 10:12pm from Washington, D.C. (IAD) Fly for 1h 3m Arrive at 11:15pm in Pittsburgh (PIT)

    Layover in Pittsburgh for 9h 35m

    Mon Jul 1st 2024 United Airlines · UA 3461 Depart at 8:50am from Pittsburgh (PIT) Fly for 1h 46m Arrive at 9:36am in Chicago (ORD)

  • USD 209
    United Airlines
    6:00am - 9:55am
    Sat Jun 29th
    4h 55m
    Washington, D.C. (IAD) → Chicago (ORD)
    1 Stop

    Sat Jun 29th 2024 United Airlines · UA 2455 Depart at 6:00am from Washington, D.C. (IAD) Fly for 1h 17m Arrive at 7:17am in New York (EWR)

    Layover in New York for 1h 3m

    Sat Jun 29th 2024 United Airlines · UA 2100 Depart at 8:20am from New York (EWR) Fly for 2h 35m Arrive at 9:55am in Chicago (ORD)

  • USD 211
    United Airlines
    10:15pm - 6:34am
    Sun Jun 30th
    9h 19m
    Washington, D.C. (IAD) → Chicago (ORD)
    1 Stop

    Sun Jun 30th 2024 United Airlines · UA 6130 Depart at 10:15pm from Washington, D.C. (IAD) Fly for 1h 43m Arrive at 11:58pm in Cincinnati (CVG)

    Layover in Cincinnati for 6h 2m

    Mon Jul 1st 2024 United Airlines · UA 3542 Depart at 6:00am from Cincinnati (CVG) Fly for 1h 34m Arrive at 6:34am in Chicago (ORD)

  • USD 211
    United Airlines
    10:15pm - 7:40am
    Sun Jun 30th
    10h 25m
    Washington, D.C. (IAD) → Chicago (ORD)
    1 Stop

    Sun Jun 30th 2024 United Airlines · UA 6130 Depart at 10:15pm from Washington, D.C. (IAD) Fly for 1h 43m Arrive at 11:58pm in Cincinnati (CVG)

    Layover in Cincinnati for 7h 12m

    Mon Jul 1st 2024 United Airlines · UA 2323 Depart at 7:10am from Cincinnati (CVG) Fly for 1h 30m Arrive at 7:40am in Chicago (ORD)

  • USD 214
    United Airlines
    10:12pm - 7:39am
    Sun Jun 30th
    10h 27m
    Washington, D.C. (IAD) → Chicago (ORD)
    1 Stop

    Sun Jun 30th 2024 United Airlines · UA 3540 Depart at 10:12pm from Washington, D.C. (IAD) Fly for 1h 3m Arrive at 11:15pm in Pittsburgh (PIT)

    Layover in Pittsburgh for 7h 45m

    Mon Jul 1st 2024 United Airlines · UA 1803 Depart at 7:00am from Pittsburgh (PIT) Fly for 1h 39m Arrive at 7:39am in Chicago (ORD)

  • USD 215
    United Airlines
    10:20pm - 6:30am
    Sat Jun 29th
    9h 10m
    Washington, D.C. (IAD) → Chicago (ORD)
    1 Stop

    Sat Jun 29th 2024 United Airlines · UA 6161 Depart at 10:20pm from Washington, D.C. (IAD) Fly for 1h 38m Arrive at 11:58pm in Detroit (DTW)

    Layover in Detroit for 6h 5m

    Sun Jun 30th 2024 United Airlines · UA 4754 Depart at 6:03am from Detroit (DTW) Fly for 1h 27m Arrive at 6:30am in Chicago (ORD)

  • USD 215
    United Airlines
    10:20pm - 8:05am
    Sat Jun 29th
    10h 45m
    Washington, D.C. (IAD) → Chicago (ORD)
    1 Stop

    Sat Jun 29th 2024 United Airlines · UA 6161 Depart at 10:20pm from Washington, D.C. (IAD) Fly for 1h 38m Arrive at 11:58pm in Detroit (DTW)

    Layover in Detroit for 7h 40m

    Sun Jun 30th 2024 United Airlines · UA 5353 Depart at 7:38am from Detroit (DTW) Fly for 1h 27m Arrive at 8:05am in Chicago (ORD)

  • USD 216
    United Airlines
    10:12pm - 7:39am
    Sat Jun 29th
    10h 27m
    Washington, D.C. (IAD) → Chicago (ORD)
    1 Stop

    Sat Jun 29th 2024 United Airlines · UA 3540 Depart at 10:12pm from Washington, D.C. (IAD) Fly for 1h 3m Arrive at 11:15pm in Pittsburgh (PIT)

    Layover in Pittsburgh for 7h 45m

    Sun Jun 30th 2024 United Airlines · UA 1803 Depart at 7:00am from Pittsburgh (PIT) Fly for 1h 39m Arrive at 7:39am in Chicago (ORD)

  • USD 216
    United Airlines
    10:12pm - 7:39am
    Fri Jun 28th
    10h 27m
    Washington, D.C. (IAD) → Chicago (ORD)
    1 Stop

    Fri Jun 28th 2024 United Airlines · UA 3540 Depart at 10:12pm from Washington, D.C. (IAD) Fly for 1h 3m Arrive at 11:15pm in Pittsburgh (PIT)

    Layover in Pittsburgh for 7h 45m

    Sat Jun 29th 2024 United Airlines · UA 1803 Depart at 7:00am from Pittsburgh (PIT) Fly for 1h 39m Arrive at 7:39am in Chicago (ORD)

  • USD 219
    United Airlines
    10:24pm - 7:36am
    Sun Jun 30th
    10h 12m
    Washington, D.C. (IAD) → Chicago (ORD)
    1 Stop

    Sun Jun 30th 2024 United Airlines · UA 2382 Depart at 10:24pm from Washington, D.C. (IAD) Fly for 1h 11m Arrive at 11:35pm in Raleigh (RDU)

    Layover in Raleigh for 6h 40m

    Mon Jul 1st 2024 United Airlines · UA 755 Depart at 6:15am from Raleigh (RDU) Fly for 2h 21m Arrive at 7:36am in Chicago (ORD)

  • USD 232
    United Airlines
    10:30pm - 6:30am
    Sun Jun 30th
    9h 0m
    Washington, D.C. (IAD) → Chicago (ORD)
    1 Stop

    Sun Jun 30th 2024 United Airlines · UA 1370 Depart at 10:30pm from Washington, D.C. (IAD) Fly for 1h 19m Arrive at 11:49pm in Cleveland (CLE)

    Layover in Cleveland for 6h 11m

    Mon Jul 1st 2024 United Airlines · UA 1421 Depart at 6:00am from Cleveland (CLE) Fly for 1h 30m Arrive at 6:30am in Chicago (ORD)

  • USD 233
    United Airlines
    10:15pm - 6:36am
    Sat Jun 29th
    9h 21m
    Washington, D.C. (IAD) → Chicago (ORD)
    1 Stop

    Sat Jun 29th 2024 United Airlines · UA 6130 Depart at 10:15pm from Washington, D.C. (IAD) Fly for 1h 43m Arrive at 11:58pm in Cincinnati (CVG)

    Layover in Cincinnati for 6h 2m

    Sun Jun 30th 2024 United Airlines · UA 5768 Depart at 6:00am from Cincinnati (CVG) Fly for 1h 36m Arrive at 6:36am in Chicago (ORD)

  • USD 235
    United Airlines
    10:30pm - 6:30am
    Sat Jun 29th
    9h 0m
    Washington, D.C. (IAD) → Chicago (ORD)
    1 Stop

    Sat Jun 29th 2024 United Airlines · UA 1370 Depart at 10:30pm from Washington, D.C. (IAD) Fly for 1h 19m Arrive at 11:49pm in Cleveland (CLE)

    Layover in Cleveland for 6h 11m

    Sun Jun 30th 2024 United Airlines · UA 1421 Depart at 6:00am from Cleveland (CLE) Fly for 1h 30m Arrive at 6:30am in Chicago (ORD)

  • USD 242
    United Airlines
    5:23pm - 11:17pm
    Sat Jun 29th
    6h 54m
    Washington, D.C. (IAD) → Chicago (ORD)
    1 Stop

    Sat Jun 29th 2024 United Airlines · UA 2398 Depart at 5:23pm from Washington, D.C. (IAD) Fly for 1h 26m Arrive at 6:49pm in New York (EWR)

    Layover in New York for 2h 51m

    Sat Jun 29th 2024 United Airlines · UA 1308 Depart at 9:40pm from New York (EWR) Fly for 2h 37m Arrive at 11:17pm in Chicago (ORD)

  • USD 302
    United Airlines
    5:33pm - 6:55pm
    Fri Jun 28th
    2h 22m
    Washington, D.C. (IAD) → Chicago (ORD)
    Direct

    Fri Jun 28th 2024 United Airlines · UA 2727 Depart at 5:33pm from Washington, D.C. (IAD) Fly for 2h 22m Arrive at 6:55pm in Chicago (ORD)

  • USD 1343
    TAP Portugal
    10:20pm - 4:15pm
    Sun Jun 30th
    18h 55m
    Washington, D.C. (IAD) → Chicago (ORD)
    1 Stop

    Sun Jun 30th 2024 TAP Portugal · TP 234 Depart at 10:20pm from Washington, D.C. (IAD) Fly for 7h 15m Arrive at 10:35am in Lisbon (LIS)

    Layover in Lisbon for 2h 30m

    Mon Jul 1st 2024 TAP Portugal · TP 243 Depart at 1:05pm from Lisbon (LIS) Fly for 9h 10m Arrive at 4:15pm in Chicago (ORD)

  • USD 1671
    TAP Portugal
    5:40pm - 4:15pm
    Sun Jun 30th
    23h 35m
    Washington, D.C. (IAD) → Chicago (ORD)
    1 Stop

    Sun Jun 30th 2024 TAP Portugal · TP 232 Depart at 5:40pm from Washington, D.C. (IAD) Fly for 7h 30m Arrive at 6:10am in Lisbon (LIS)

    Layover in Lisbon for 6h 55m

    Mon Jul 1st 2024 TAP Portugal · TP 243 Depart at 1:05pm from Lisbon (LIS) Fly for 9h 10m Arrive at 4:15pm in Chicago (ORD)

  • USD 1944
    TAP Portugal
    5:10pm - 4:10pm
    Sat Jun 29th
    24h 0m
    Washington, D.C. (IAD) → Chicago (ORD)
    1 Stop

    Sat Jun 29th 2024 TAP Portugal · TP 232 Depart at 5:10pm from Washington, D.C. (IAD) Fly for 7h 30m Arrive at 5:40am in Lisbon (LIS)

    Layover in Lisbon for 7h 10m

    Sun Jun 30th 2024 TAP Portugal · TP 243 Depart at 12:50pm from Lisbon (LIS) Fly for 9h 20m Arrive at 4:10pm in Chicago (ORD)

@sarahbb1
Sarah Belizaire
@sarahbb1

Have flexible travel plans or looking for alternative routes given the chaos? Check out all the connection possibilities via a super helpful site created by @ismaelyws flightlist.io thanks to @andy_travels for the recommendation #travel #flights

@eyupitsjohn
John Ford
@eyupitsjohn

There seem to be lots of sites launching at the moment that promise to find you cheap flights but not many have the professional finish of Flightlist by @ismaelyws #travel #flights

@andy_travels
Andy Travels
@andy_travels

@ismaelyws Just tried out Flightlist for the first time. Really nice idea, well made, and just what I need at the moment 👍

@travelwitbender
Travel With Bender
@travelwitbender

Did you spot my recent article about how to score cheap one way flights? ✈️ FlightList is my new secret tool for discovering cheap routes, within a departure date range. Plus you can also search by country/region for departures & destinations. Powerful! 💪

Explore Flight Options

Cheap Flight Search Tips

Tips to help you find the cheapest flights from Washington to Chicago (IAD to CHI).

  • Book 45-90 days before your departure date.
  • Fly during weekdays (Monday-Thursday).
  • Airfare Sales: Airlines sometimes offer huge discounts and since we take a bottom-up approach these flights will appear first in the results, so check back regularly because they don't usually last long.

Why I Built FlightList

❝As someone who works remotely & travels frequently, I always book one way flights and I'm flexible on my departure dates. I look for the best deals. Most sites require you to enter a specific departure date and clutter the page with uneccessary options, images and ads. I want something simple and minimal which allows me to search by departure date range & display a list of flights with the ability to filter according to my needs. So, I built FlightList to solve my own problem & help other travelers who may have the same frustration. It's how I imagine a flight booking site should be.❞

- Hans Desjarlais, Founder & Creator Hans Desjarlais