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Cheap flights from Washington Ronald Reagan to Chicago Midway

Compare Washington Ronald Reagan to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from Washington Ronald Reagan to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Washington Ronald Reagan to Chicago Midway? Find the lowest prices on one-way and return tickets right here.
Chicago.P11,939 per passenger.Departing Sat, 17 Jan, returning Sun, 18 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Sat, 17 Jan, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 18 Jan, arriving in Washington Ronald Reagan.Price includes taxes and charges.From P11,939, select.
Chicago.P12,983 per passenger.Departing Sat, 11 Apr, returning Sat, 18 Apr.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Sat, 11 Apr, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 18 Apr, arriving in Washington Ronald Reagan.Price includes taxes and charges.From P12,983, select.
Chicago.P12,983 per passenger.Departing Sat, 28 Mar, returning Sat, 11 Apr.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Sat, 28 Mar, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 11 Apr, arriving in Washington Ronald Reagan.Price includes taxes and charges.From P12,983, select.
Chicago.P13,057 per passenger.Departing Wed, 31 Dec, returning Thu, 1 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Wed, 31 Dec, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 1 Jan, arriving in Washington Ronald Reagan.Price includes taxes and charges.From P13,057, select.
Chicago.P13,221 per passenger.Departing Wed, 18 Feb, returning Sat, 21 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Wed, 18 Feb, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 21 Feb, arriving in Washington Ronald Reagan.Price includes taxes and charges.From P13,221, select.
Chicago.P13,454 per passenger.Departing Sat, 24 Jan, returning Tue, 3 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Sat, 24 Jan, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 3 Feb, arriving in Washington Ronald Reagan.Price includes taxes and charges.From P13,454, select.
Chicago.P14,639 per passenger.Departing Wed, 11 Mar, returning Mon, 16 Mar.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Wed, 11 Mar, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 16 Mar, arriving in Washington Ronald Reagan.Price includes taxes and charges.From P14,639, select.
Chicago.P15,322 per passenger.Departing Sat, 1 Aug, returning Wed, 5 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Sat, 1 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 5 Aug, arriving in Washington Ronald Reagan.Price includes taxes and charges.From P15,322, select.

Find the cheapest month to fly from Washington Ronald Reagan to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Washington Ronald Reagan to Chicago Midway flights are currently cheapest in January.
Dec
from P18,340
Jan
from P11,939
Feb
from P13,221
Mar
from P14,639
Apr
from P12,983
May
from P15,743
Jun
from P15,752
Jul
from P15,763
Aug
from P15,322
Sep
from P15,668
Oct
Find prices
Nov
Find prices

Direct flights from Washington Ronald Reagan to Chicago Midway

Washington Ronald Reagan to Chicago Midway: Alternative routes

Compare routes from Washington Ronald Reagan to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Washington D.C. to Chicago: Flight information

The things to know before you go.
Cheapest flight foundP11,939
Cheapest month to flyJanuary
Average flight time2 hrs, 6 mins
Most popular airlineSouthwest Airlines
Average flights per week45

Finding cheap flights from Washington Ronald Reagan to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Washington Ronald Reagan to Chicago Midway is P11,939. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 6 minutes is the average flight time from Washington Ronald Reagan to Chicago Midway.
Southwest Airlines flies direct from Washington Ronald Reagan to Chicago Midway.
As of December 2025, there are 45 flights per week flying from Washington Ronald Reagan to Chicago Midway.
The cheapest month to fly from Washington Ronald Reagan to Chicago Midway is usually January.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Washington Ronald Reagan Airport to Chicago Midway Airport on Saturday, 17 January 2026.
Yes – the average flight time is 2 hours and 6 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Southwest Airlines offers the cheapest flight tickets to Chicago Midway.

Travelling from Ronald Reagan National Airport (DCA) to Chicago Midway International Airport (MDW): what you need to know

  • Around 2 hours 5 minutes is how long you can expect to be in the air on a direct flight from Ronald Reagan National Airport to Chicago Midway International Airport.

  • The timezone in Chicago is UTC-5, which is one hour behind Washington DC.

  • Flights from DCA to MDW start at 06:00 — the earliest with Southwest Airlines. The latest departure is at 21:35 with Southwest Airlines. Overall, you can choose from 30 weekly Ronald Reagan National Airport to Chicago Midway International Airport flights.

  • To ensure you catch your DCA to MDW flight, allow plenty of time to check in and find your gate. Turning up two hours before international departures and an hour before domestic flights is the general rule.

  • During popular months like February, you'll want to get to the airport even earlier. Plan to arrive two hours before a domestic departure and four hours ahead of international flights when you fly during a high season in general.

  • Southwest Airlines has direct flights from Ronald Reagan National Airport to Chicago Midway International Airport. Book with this popular airline, then get ready to check out the sights in Chicago — and maybe even more of United States if your schedule allows.

  • The majority of passengers choose to travel with Southwest Airlines on this route.

  • With 78.68% of services landing as planned, Southwest Airlines is the most punctual carrier offering DCA to MDW flights.

  • Consider adding a stopover when booking your ticket from Ronald Reagan National Airport to Chicago Midway International Airport. Just uncheck 'Direct flights only' to break up your trip, or maybe even explore a new city along the way. Here's where you can stop between DCA and MDW:

    • John Glenn Columbus International Airport

    • Detroit Metropolitan Wayne County Airport

    • Cleveland Hopkins International Airport

How to find the cheapest flights from Ronald Reagan National Airport (DCA) to Chicago Midway International Airport (MDW)

  • Currently, P5,074 is the lowest price we've found for a one-way Ronald Reagan National Airport to Chicago Midway International Airport flight. The best price for a return plane ticket is P11,939. Bear in mind that fares may change due to availability when booking.

  • To score cheap tickets from DCA to MDW, book your trip eight months before your planned departure.

  • July is the cheapest month for flights from Ronald Reagan National Airport to Chicago Midway International Airport. If you need to fly during a different time of year, the 'Whole month' tool will give you the lowest airfares for every month.

  • You won't have to check every day to find out if fares have dropped when you set up a Price Alert. We'll notify you the moment a special offer becomes available on cheap flights from DCA to MDW.

  • Pick your preferred arrival and departure times, airlines and number of stops with the filters. Alternatively, sort your results by 'Cheapest' to get the best deals on flights from Ronald Reagan National Airport to Chicago Midway International Airport.

Handy information about Ronald Reagan National Airport (DCA)

  • You'll find DCA at 1 Aviation Circle.

  • When it comes to the on-time performance of Ronald Reagan National Airport, 76.44% of flights stick to their scheduled arrival time.

  • Central Washington DC to Ronald Reagan National Airport is around 8 kilometres. Depending on traffic, it'll take you about 15 minutes to get there if you're catching a cab, ride-sharing or driving.

  • The trip when using public transport takes about 45 minutes.

  • Booked an early flight from Ronald Reagan National Airport to Chicago Midway International Airport? Avoid the last-minute rush to the terminal (and get some extra shut-eye) by picking one of these hotels near DCA:

Arriving at Chicago Midway International Airport (MDW)

  • The last thing you need is a long journey to your hotel if you're getting in late on a Ronald Reagan National Airport to Chicago Midway International Airport flight. Stay at one of these accommodation options near MDW instead:

  • Grab a Chicago Midway International Airport rental car and explore Chicago and beyond with your own wheels. Dollar, Hertz and Budget are popular outlets you can book with here.

  • Secure the lowest price by booking your ride from Chicago Midway International Airport around four weeks ahead of your departure.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • You'll find MDW at 5700 South Cicero.

  • Chicago Midway International Airport to central Chicago has a drive time of about 20 minutes. It's approximately 19 kilometres away.

  • Getting there on public transport typically takes 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

  • It's time to work out your travel dates for your flight from Ronald Reagan National Airport to Chicago Midway International Airport. July is the busiest month to head to Chicago. If you prefer a quieter vibe, go in May.

  • When booking your flight from Ronald Reagan National Airport to Chicago Midway International Airport, think about the type of weather you like. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • January has average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Search for cheap tickets from DCA to MDW around that time if you'd rather travel in cooler conditions.

Explore more of United States

  • Columbus is just one of the many cities in United States waiting to be discovered once you've seen the sights of Chicago. Around 451 kilometres away to the south-east, its top attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another essential stop in United States. Experience this destination's highlights firsthand at The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Plan the rest of your trip from Washington D.C. to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.