From $71, Book Cheap Flights from Washington, DC to Chicago

This time, your Chicago travel is no more expensive when you believe in cheap flight ticket booking ideas and tips. Here are some significant things you need to know about the cheap flights from Washington, DC, to Chicago. Therefore, make sure to pay attention to all the cost-effective deals for you. Thus, check all the significant facts and tips to know. American, Southwest, and United Airlinesare the three major airlines that offer direct service for this route.

First, pre-booking is a vital topic you can't ignore. Flyingscanner is the leading website for finding cheap flights to Chicago. You can also manage your trip booking with us in pre-booking mode. How far in advance do you need to book airline tickets? You need to book the tickets at least 4 to 5 months before your Chicago travel departure date.

When we compare the airfare from Washington, DC to Chicago, we can see that the west is a low-cost option and often the cheapest for passengers. You can find the best deals with Southwest Airlines' low-cost airfare. These are the key things you need to know about this route, because sometimes you may need to avoid booking luxurious airlines like Delta or United to save on airfare.

Capital to Windy City: A Classic Skyline-to-Skyline Hop

• Departure: Washington Dulles International (IAD), Reagan National (DCA), or Baltimore/Washington (BWI)
• Arrival: O'Hare International (ORD), Midway International (MDW), Chicago
• Distance: Approx. 595 miles (957 km)
• Average Duration: Approx. 1 hr 55 mins (non-stop)

Direct Flight Providers:

• American Airlines
• United Airlines
• Southwest Airlines

Typical Pricing (Booking Ahead 8 Weeks):

• One-Way: Approx. $70 – $160
• Round-Trip: Approx. $140 – $280

When to Book for Best Prices:

• Book flights 3 to 5 weeks in advance
• Mid-week flights (Tuesday & Wednesday) are generally more affordable

Peak and Off-Peak Travel:

• Peak Season: May to September
• Off-Peak Season: January to March

Transportation from Arrival Airport to City:

• From ORD: CTA Blue Line (~45 mins to downtown)
• From MDW: CTA Orange Line (~25 mins to downtown)

Other Airport Options:

Alternate Departure Point:

• Baltimore/Washington International (BWI)

Alternate Arrival Point:

• Midway International Airport (MDW), Chicago

Set fare alerts to know about the best deals

Exclusive, cheap discount deals are available when you use and set the fare alert for the reservations. A fare alert is crucial because you can't find the most affordable airfare packages for your booking if you don't do this. Thus, pay attention to all the best deals with the help of fare alerts.

Know the hacks to save more on Chicago trips.

Hacks are essential to follow, and it's not easy to find deals when you're not following them. Therefore, first, know about the cheapest day to fly, Thursday, because Sundays were expensive to buy cheap flights from Washington DC to Chicago. Knowing about all those deals available on an affordable day is essential.

Compare the airfare of major airlines on different dates, as flexible travel dates can help you find the best deals. You must be adaptable to the arrival and departure dates to take advantage of the great offers. If you choose the wrong travel dates, you may have to pay extra for your reservations.

Search for cheap tickets from Washington, DC to Chicago in the browser's private mode, as this is the best way to manage trip booking. Your history and cookies will not be saved, and you will get the updated fare alerts.

Manage your booking online, as it's a time-saving and practical approach to finding great deals. You can also check the best deals with the pre-booking idea.

Ronald Reagan Washington National Airport (DCA) to Chicago O'Hare International Airport (ORD): Alternative routes

Cheapest vs Fastest Option

Options	Price (one way)	Time	Airlines
Nonstop (DCA→ORD)	$89–$299	2 hours 15 minutes	American/United
1-Stop (DCA→CLT→ORD)	$79–$249	4-5 hours	American
1-Stop (DCA→EWR→ORD)	$69–$199	5-6 hours	United

Alternative Airports (Chicago Area)

Options	Price (one way)	Time	Transport to Downtown
Direct (DCA → MDW)	$99–$229	2.5 hours + 30 min train	Orange Line ($3)
1-Stop (DCA→DTW→ORD)	$89–$209	5 hours total	Delta Sky Club access

FAQs

What is the lowest starting price for flights on this route?

One-way flights usually start at $71, especially when booked in advance.

When is the best time to book for cheaper fares?

Book flights 3 to 5 weeks in advance, and look for departures on Tuesdays or Wednesdays for the best prices.

Which day is the cheapest to fly?

Thursday is often the cheapest day to fly, while Sunday tends to be more expensive.

Which airlines offer low-cost options?

Southwest Airlines is a popular low-cost carrier that often provides the most affordable fares on this route.

How can I save more when booking flights?

Use fare alerts, compare prices on flexible dates, search in private mode, and avoid last-minute bookings for better deals.