$89+ Cheap flights from Reagan-National (DCA) to Midway (MDW)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
DCA — MDW
Sep 5 — Sep 121
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 September or March, booked 52 days in advance, depart on a Saturday or Wednesday and return on a Wednesday
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 August 6, 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 August 6, 2026.
This Southwest deal was found by Cheapflights users on 8/5. 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 9/56:00 am -
2 stops8h 20m
Sun 9/65:55 am -
Nonstop1h 45m
Deal found 8/5![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 8/1. 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.
Sat 9/56:00 am -
2 stops8h 20m
Fri 9/112:50 pm -
1 stop6h 05m
Deal found 8/1![Southwest logo]()
$202
This Southwest deal was found by Cheapflights users on 8/4. 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 9/119:15 pm -
Nonstop2h 00m
Mon 9/149:00 pm -
Nonstop1h 55m
Deal found 8/4![Southwest logo]()
$216
This Southwest deal was found by Cheapflights users on 8/3. 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 9/117:25 am -
Nonstop1h 55m
Tue 9/158:40 am -
2 stops6h 10m
Deal found 8/3![Southwest logo]()
$231
This Delta deal was found by Cheapflights users on 8/1. 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.
Sat 9/510:10 am -
1 stop6h 34m
Sun 9/66:05 am -
1 stop5h 40m
Deal found 8/1![Delta logo]()
$238
This Southwest deal was found by Cheapflights users on 8/3. 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 9/116:50 pm -
1 stop4h 10m
Sat 9/127:55 am -
2 stops8h 00m
Deal found 8/3![Southwest logo]()
$241
This Southwest deal was found by Cheapflights users on 8/4. 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.
Thu 9/39:10 am -
Nonstop2h 00m
Sat 9/51:20 pm -
Nonstop1h 55m
Deal found 8/4![Southwest logo]()
$242
This Southwest deal was found by Cheapflights users on 8/4. 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 9/49:15 pm -
Nonstop2h 00m
Sun 9/68:10 am -
Nonstop2h 00m
Deal found 8/4![Southwest logo]()
$245
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 August 6, 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 August 6, 2026.
This Southwest deal was found by Cheapflights users on 8/3. 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 9/121:00 pm -
Nonstop1h 55m
Mon 9/149:00 pm -
Nonstop1h 55m
Deal found 8/3![Southwest logo]()
$255
This Delta deal was found by Cheapflights users on 8/5. 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.
Thu 10/16:10 am -
1 stop3h 57m
Wed 10/71:27 pm -
1 stop4h 10m
Deal found 8/5![Delta logo]()
$275
This Southwest deal was found by Cheapflights users on 8/4. 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.
Thu 9/39:10 am -
Nonstop2h 00m
Sat 9/57:55 am -
2 stops6h 05m
Deal found 8/4![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 8/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:10 am -
1 stop4h 07m
Mon 10/196:44 pm -
1 stop3h 23m
Deal found 8/4![Delta logo]()
$275
This Southwest deal was found by Cheapflights users on 8/3. 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 9/27:00 pm -
1 stop4h 20m
Mon 9/75:45 am -
Nonstop1h 45m
Deal found 8/3![Southwest logo]()
$265
This Southwest deal was found by Cheapflights users on 8/1. 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 8/318:15 am -
1 stop5h 00m
Mon 9/75:45 am -
Nonstop1h 45m
Deal found 8/1![Southwest logo]()
$265
This Delta deal was found by Cheapflights users on 8/1. 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.
Wed 10/146:00 am -
1 stop5h 03m
Fri 10/166:44 pm -
1 stop3h 23m
Deal found 8/1![Delta logo]()
$304
This Southwest deal was found by Cheapflights users on 8/3. 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 9/166:00 am -
2 stops7h 05m
Tue 9/2210:10 am -
1 stop5h 00m
Deal found 8/3![Southwest logo]()
$280
This Southwest deal was found by Cheapflights users on 8/5. 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 9/49:15 pm -
Nonstop2h 00m
Wed 9/94:15 pm -
Nonstop1h 55m
Deal found 8/5![Southwest logo]()
$284
This Southwest deal was found by Cheapflights users on 8/5. 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 10/79:00 pm -
Nonstop1h 55m
Sun 10/114:45 pm -
Nonstop1h 50m
Deal found 8/5![Southwest logo]()
$312
This Southwest deal was found by Cheapflights users on 8/4. 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.
Wed 11/42:40 pm -
1 stop4h 05m
Sun 11/812:25 pm -
Nonstop1h 50m
Deal found 8/4![Southwest logo]()
$318
Last-minute flights from Reagan-National to MidwayDiscover last-minute flight deals from Reagan-National to Midway. Data last updated August 6, 2026 and is based on user searches.
Discover last-minute flight deals from Reagan-National to Midway. Data last updated August 6, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/4. 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.
Thu 9/39:10 am -
Nonstop2h 00m
Sat 9/51:20 pm -
Nonstop1h 55m
Deal found 8/4![Southwest logo]()
$242
This Southwest deal was found by Cheapflights users on 8/5. 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 9/49:15 pm -
Nonstop2h 00m
Sun 9/68:10 am -
Nonstop2h 00m
Deal found 8/5![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 8/5. 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 9/56:00 am -
2 stops8h 20m
Sun 9/65:55 am -
Nonstop1h 45m
Deal found 8/5![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 8/3. 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.
Sun 9/66:00 am -
1 stop4h 40m
Sun 9/610:50 am -
1 stop6h 10m
Deal found 8/3![Southwest logo]()
$254
This Southwest deal was found by Cheapflights users on 8/6. 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 9/113:35 pm -
Nonstop2h 05m
Tue 9/158:25 am -
Nonstop2h 00m
Deal found 8/6![Southwest logo]()
$216
This Southwest deal was found by Cheapflights users on 8/6. 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 9/114:35 pm -
1 stop4h 35m
Mon 9/145:45 am -
Nonstop1h 45m
Deal found 8/6![Southwest logo]()
$226
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 August 6, 2026.
Search for one-way flight options from Reagan-National to Midway. Find affordable one-way fares based on user searches. Data last updated August 6, 2026.
This Southwest deal was found by Cheapflights users on 8/4. 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.
Sat 9/53:40 pm -
Nonstop2h 10m
Deal found 8/4![Southwest logo]()
$89
This Delta deal was found by Cheapflights users on 8/5. 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.
Sat 9/512:33 pm -
1 stop5h 26m
Deal found 8/5![Delta logo]()
$99
This Southwest deal was found by Cheapflights users on 8/6. 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 9/16:40 pm -
Nonstop1h 55m
Deal found 8/6![Southwest logo]()
$128
This Southwest deal was found by Cheapflights users on 8/4. 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.
Tue 11/32:40 pm -
1 stop4h 05m
Deal found 8/4![Southwest logo]()
$133
This Southwest deal was found by Cheapflights users on 8/5. 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 9/28:00 am -
1 stop6h 55m
Deal found 8/5![Southwest logo]()
$138
This Southwest deal was found by Cheapflights users on 8/2. 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.
Sat 10/176:15 am -
2 stops9h 35m
Deal found 8/2![Southwest logo]()
$149
This Southwest deal was found by Cheapflights users on 8/4. 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.
Wed 12/3011:50 am -
Nonstop2h 05m
Deal found 8/4![Southwest logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:00 am -
2 stops15h 53m
Deal found 8/4![Frontier logo]()
$153
This Southwest deal was found by Cheapflights users on 8/4. 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.
Thu 9/39:10 am -
Nonstop2h 00m
Deal found 8/4![Southwest logo]()
$154
This Southwest deal was found by Cheapflights users on 8/5. 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 9/49:15 pm -
Nonstop2h 00m
Deal found 8/5![Southwest logo]()
$157
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 August 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $197 (Delta) |
One-way from | $89 (Southwest) |
Popular in | August |
Cheapest in | September |
Average price | $590 |
Good round-trip deal | $271 or less |
Good one-way deal | $177 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 2,558,603 searches. Data last updated August 6, 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
Sat 9/12
1:00 pm-1:55 pm
Nonstop1h 55m
Chicago Midway
Mon 9/14
9:00 pm-11:55 pm
Nonstop1h 55m
$255
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Thu 9/3
9:10 am-10:10 am
Nonstop2h 00m
Chicago Midway
Sat 9/5
7:55 am-3:00 pm
2 stops6h 05m
$257
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Wed 9/2
7:00 pm-10:20 pm
1 stop4h 20m
Chicago Midway
Mon 9/7
5:45 am-8:30 am
Nonstop1h 45m
$265
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Mon 8/31
8:15 am-12:15 pm
1 stop5h 00m
Chicago Midway
Mon 9/7
5:45 am-8:30 am
Nonstop1h 45m
$265
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Thu 10/1
6:10 am-9:07 am
1 stop3h 57m
Chicago Midway
Wed 10/7
1:27 pm-6:37 pm
1 stop4h 10m
$275
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Thu 10/15
6:10 am-9:17 am
1 stop4h 07m
Chicago Midway
Mon 10/19
6:44 pm-11:07 pm
1 stop3h 23m
$275
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Wed 9/16
6:00 am-12:05 pm
2 stops7h 05m
Chicago Midway
Tue 9/22
10:10 am-4:10 pm
1 stop5h 00m
$280
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Fri 9/4
9:15 pm-10:15 pm
Nonstop2h 00m
Chicago Midway
Wed 9/9
4:15 pm-7:10 pm
Nonstop1h 55m
$284
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Wed 10/14
6:00 am-10:03 am
1 stop5h 03m
Chicago Midway
Fri 10/16
6:44 pm-11:07 pm
1 stop3h 23m
$304
Quickest round-trip
Washington, D.C.Chicago
DCA Washington, D.C. Reagan-National - MDW Chicago Midway
DCAMDW
Washington, D.C. Reagan-National
Wed 10/7
9:00 pm-9:55 pm
Nonstop1h 55m
Chicago Midway
Sun 10/11
4:45 pm-7:35 pm
Nonstop1h 50m
$312
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 August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 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, September is the cheapest month in which you can book a flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport (average of $267). Flying from Washington, D.C. Reagan-National Airport to Chicago Midway Airport in August is currently the most expensive (average of $590). 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 August 6, 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 20% 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 August 1, 2026.
Travelers seeking maximum savings on their Washington, D.C. Reagan-National Airport to Chicago Midway Airport flight should consider departing on Tuesday 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 August 6, 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
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
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?
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Reagan-National and Midway flights
Browse other Reagan-National and Midway flight options. Last updated on August 6, 2026.
Other flights from Reagan-National
Browse through other flights departing from Reagan-National. Flights are based on user searches made on Cheapflights and were last updated on August 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 2,558,603 searches. Data last updated August 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$221 | Average$368 | FlexibilityNo cancel fee | On-time63% |