$139+ Cheap flights from Reagan-National (DCA) to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
DCA — MDW
Dec 4 — Dec 111
Round-trip
1 adult, Economy
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Find cheap flights from Reagan-National to Midway with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Washington, D.C. Reagan-National to Chicago Midway are usually found in March or February, booked 60 days in advance, depart on a Saturday or Wednesday and return on a Saturday
Cheap flight deals from Reagan-National to Midway
Cheapest
Best
Last-minute
One-way
Cheapest flights from Reagan-National to MidwayExplore the most affordable flight options available from Reagan-National to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2026.
Explore the most affordable flight options available from Reagan-National to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2026.
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/311:00 am -
Nonstop2h 05m
Mon 12/74:15 pm -
Nonstop1h 45m
Deal found 11/3![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:45 am -
1 stop4h 06m
Thu 11/2611:05 am -
1 stop9h 55m
Deal found 11/3![Delta logo]()
$280
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/188:25 am -
1 stop7h 20m
Wed 12/235:35 am -
Nonstop1h 50m
Deal found 11/2![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/32:40 pm -
1 stop4h 10m
Thu 12/1011:30 am -
1 stop6h 25m
Deal found 11/2![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/11:35 pm -
1 stop7h 05m
Thu 12/109:15 am -
Nonstop1h 45m
Deal found 11/3![Southwest logo]()
$293
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/19:45 am -
1 stop4h 16m
Sat 12/511:28 am -
1 stop4h 58m
Deal found 11/3![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/102:40 pm -
1 stop4h 10m
Tue 12/1510:20 am -
2 stops7h 30m
Deal found 11/2![Southwest logo]()
$298
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/512:15 pm -
2 stops8h 20m
Mon 12/78:15 am -
1 stop4h 50m
Deal found 10/31![Southwest logo]()
$302
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/102:40 pm -
1 stop4h 10m
Sat 12/126:35 am -
2 stops11h 50m
Deal found 11/2![Southwest logo]()
$303
This Southwest deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:25 am -
1 stop6h 45m
Fri 11/275:30 am -
1 stop6h 00m
Deal found 11/1![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/186:10 am -
Nonstop2h 05m
Thu 12/317:25 am -
Nonstop1h 50m
Deal found 11/4![Southwest logo]()
$308
Best flights from Reagan-National to MidwayDiscover carefully curated flight deals from Reagan-National to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
Discover carefully curated flight deals from Reagan-National to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/159:35 pm -
Nonstop2h 05m
Tue 1/196:00 am -
Nonstop1h 55m
Deal found 10/30![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/227:43 pm -
1 stop5h 12m
Mon 1/251:41 pm -
1 stop3h 53m
Deal found 11/1![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/258:25 am -
1 stop4h 40m
Wed 12/308:55 pm -
Nonstop1h 45m
Deal found 10/31![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/256:10 am -
Nonstop2h 05m
Thu 12/318:15 am -
1 stop4h 50m
Deal found 10/31![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/101:00 pm -
Nonstop2h 15m
Mon 12/148:15 am -
1 stop4h 50m
Deal found 11/3![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/279:35 am -
Nonstop2h 10m
Mon 2/18:40 am -
1 stop4h 55m
Deal found 11/3![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/216:45 pm -
Nonstop2h 15m
Sun 1/248:25 am -
Nonstop2h 00m
Deal found 11/2![Southwest logo]()
$318
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/142:40 pm -
1 stop4h 10m
Mon 12/215:10 pm -
Nonstop1h 45m
Deal found 10/30![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/207:40 pm -
1 stop5h 40m
Fri 12/253:50 pm -
1 stop5h 20m
Deal found 11/2![Southwest logo]()
$338
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:55 pm -
1 stop5h 05m
Tue 11/2412:50 pm -
2 stops7h 55m
Deal found 10/30![Southwest logo]()
$353
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/191:55 pm -
2 stops7h 15m
Sat 12/265:30 am -
Nonstop1h 50m
Deal found 11/3![Southwest logo]()
$374
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/142:35 pm -
Nonstop2h 05m
Mon 11/237:20 am -
Nonstop1h 50m
Deal found 10/30![Southwest logo]()
$379
Last-minute flights from Reagan-National to MidwayDiscover last-minute flight deals from Reagan-National to Midway. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Reagan-National to Midway. Data last updated November 4, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:25 am -
1 stop6h 45m
Fri 11/275:30 am -
1 stop6h 00m
Deal found 11/1![Southwest logo]()
$307
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:45 am -
1 stop4h 06m
Thu 11/2611:05 am -
1 stop9h 55m
Deal found 11/3![Delta logo]()
$280
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/11:35 pm -
1 stop7h 05m
Thu 12/109:15 am -
Nonstop1h 45m
Deal found 11/3![Southwest logo]()
$293
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/19:45 am -
1 stop4h 16m
Tue 12/16:41 pm -
1 stop3h 53m
Deal found 11/3![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/311:00 am -
Nonstop2h 05m
Mon 12/77:25 am -
Nonstop1h 50m
Deal found 11/3![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/32:40 pm -
1 stop4h 10m
Thu 12/1011:30 am -
1 stop6h 25m
Deal found 11/2![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/512:15 pm -
2 stops8h 20m
Mon 12/78:15 am -
1 stop4h 50m
Deal found 10/31![Southwest logo]()
$302
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/102:40 pm -
1 stop4h 10m
Tue 12/1510:20 am -
2 stops7h 30m
Deal found 11/2![Southwest logo]()
$298
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/102:40 pm -
1 stop4h 10m
Sat 12/126:35 am -
2 stops11h 50m
Deal found 11/2![Southwest logo]()
$303
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/188:25 am -
1 stop7h 20m
Wed 12/235:35 am -
Nonstop1h 50m
Deal found 11/2![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/186:10 am -
Nonstop2h 05m
Thu 12/317:25 am -
Nonstop1h 50m
Deal found 11/4![Southwest logo]()
$308
One-way flights from Reagan-National to MidwaySearch for one-way flight options from Reagan-National to Midway. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
Search for one-way flight options from Reagan-National to Midway. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:55 pm -
Nonstop2h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Southwest logo]()
$139
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/152:40 pm -
1 stop4h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Southwest logo]()
$144
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:45 am -
1 stop4h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Delta logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:00 am -
2 stops29h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Frontier logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:00 pm -
2 stops42h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$151
This Kissandfly.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/111:40 pm -
2 stops22h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$153
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/214:40 pm -
1 stop4h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Southwest logo]()
$159
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1712:00 pm -
2 stops6h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Southwest logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:00 am -
2 stops27h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$165
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/186:10 am -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Southwest logo]()
$170
Find flight deals from Reagan-National to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Reagan-National (DCA) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $263 (Delta) |
One-way from | $139 (Southwest) |
Popular in | June |
Cheapest in | March |
Average price | $383 |
Good round-trip deal | $327 or less |
Good one-way deal | $180 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Reagan-National to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 4, 2026.
Use the filters below to find and compare flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Tue 12/15
8:55 pm-10:10 pm
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
Quickest round-trip
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Thu 12/17
10:45 am-11:50 am
Nonstop2h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Wed 12/23
9:00 pm-10:05 pm
Nonstop2h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Fri 11/27
6:30 pm-7:40 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Fri 12/4
2:40 pm-5:50 pm
1 stop4h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$144
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Wed 12/23
6:00 am-8:49 am
1 stop3h 49m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Sat 11/21
9:45 am-12:51 pm
1 stop4h 06m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Fri 12/18
8:25 am-2:45 pm
1 stop7h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Mon 12/7
6:50 pm-8:00 pm
Nonstop2h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$179
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Wed 11/25
7:40 pm-12:20 am
1 stop5h 40m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$180
Showing 1-10 of 22 resultsSorted by cheapest first
Compare providers for flights from Reagan-National to Midway
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Reagan-National to Midway in November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Washington, D.C. Reagan-National Airport-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Washington, D.C. Reagan-National Airport-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Washington, D.C. Reagan-National Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Washington, D.C. Reagan-National Airport-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Washington, D.C. Reagan-National Airport-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Reagan-National to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Reagan-National with our price prediction graph.
DCA-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport
How far ahead should I book a flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?
To ensure you get the cheapest price possible for a flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport, you should look to book at least 46 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.
What is the cheapest month to book a flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?
Currently, March is the cheapest month in which you can book a flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport (average of $316). Flying from Washington, D.C. Reagan-National Airport to Chicago Midway Airport in June is currently the most expensive (average of $478). 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.
What is the cheapest time of day to fly from DCA to MDW?
Find hourly flight availability from Reagan-National to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 4, 2026.
One of the essential ways to save on airfare from Washington, D.C. Reagan-National Airport to Chicago Midway Airport is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 14% on airfare.
What is the cheapest day to fly from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from Reagan-National to Midway. Price data was last updated on October 31, 2026.
Travelers seeking maximum savings on their Washington, D.C. Reagan-National Airport to Chicago Midway Airport flight should consider departing on Wednesday at noon when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Washington, D.C. Reagan-National Airport to Chicago Midway Airport flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Washington, D.C. Reagan-National Airport to Chicago Midway Airport trip
Our travel experts
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated November 4, 2026.
Get a feel of what it's like to fly with Southwest from Washington, D.C. Reagan-National Airport to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Reagan-National to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Top airline flying from Reagan-National to Midway
Discover the top airline that operate flights from Reagan-National to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$227 | Average$382 | FlexibilityNo cancel fee | On-time63% |