$73 Cheap flight deals from Chicago (CHI) to Leesburg (WAS)

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This Weekend's Flight Deals from Chicago to Leesburg

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Apr 18 - Mon, Apr 20
ORD
O'Hare Intl.
IAD
Washington Dulles Intl.
$224 Roundtrip, found 5 hours ago
$224
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sat, Apr 18 from O'Hare Intl. to Washington Dulles Intl., returning Mon, Apr 20, priced at $224 found 5 hours ago
Sun, Apr 19 - Tue, Apr 21
MDW
Midway Intl.
IAD
Washington Dulles Intl.
$335 Roundtrip, found 6 days ago
$335
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sun, Apr 19 from Midway Intl. to Washington Dulles Intl., returning Tue, Apr 21, priced at $335 found 6 days ago
Fri, Apr 17 - Sun, Apr 19
ORD
O'Hare Intl.
DCA
Ronald Reagan Washington National
$376 Roundtrip, found 4 hours ago
$376
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Fri, Apr 17 from O'Hare Intl. to Ronald Reagan Washington National, returning Sun, Apr 19, priced at $376 found 4 hours ago
Sat, Apr 18 - Mon, Apr 20
MDW
Midway Intl.
DCA
Ronald Reagan Washington National
$605 Roundtrip, found 5 hours ago
$605
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sat, Apr 18 from Midway Intl. to Ronald Reagan Washington National, returning Mon, Apr 20, priced at $605 found 5 hours ago

Airfares from $73 One Way, $140 Round Trip from Chicago to Leesburg

Prices starting at $140 for return flights and $73 for one-way flights to Leesburg were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, May 2 - Wed, May 6
MDW
Chicago
IAD
Washington
$140 Roundtrip, found 4 days ago
$140
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, May 2 from Chicago to Washington, returning Wed, May 6, priced at $140 found 4 days ago
Mon, May 4 - Thu, May 7
ORD
Chicago
IAD
Washington
$140 Roundtrip, found 1 day ago
$140
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, May 4 from Chicago to Washington, returning Thu, May 7, priced at $140 found 1 day ago
Sat, May 9 - Tue, May 12
ORD
Chicago
IAD
Washington
$142 Roundtrip, found 7 hours ago
$142
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sat, May 9 from Chicago to Washington, returning Tue, May 12, priced at $142 found 7 hours ago
Sat, May 2 - Sun, May 3
ORD
Chicago
IAD
Washington
$160 Roundtrip, found 6 hours ago
$160
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Sat, May 2 from Chicago to Washington, returning Sun, May 3, priced at $160 found 6 hours ago
Tue, Jun 9 - Tue, Jun 16
ORD
Chicago
DCA
Washington
$177 Roundtrip, found 5 days ago
$177
Roundtrip
found 5 days ago
Select United flight, departing Tue, Jun 9 from Chicago to Washington, returning Tue, Jun 16, priced at $177 found 5 days ago

Leesburg economy flight packages

Price found within the past 48 hours. Click for updated prices.
Kellogg Conference Hotel at Gallaudet University
3.0-star property

Kellogg Conference Hotel at Gallaudet University

8.2/10 Very Good! (1,004 reviews)

May 15 - May 18

3 night stay

Chicago (CHI) to Washington (DCA)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $996, price is now $649 per person
$649
per person
found 2 hours ago
Although our stay here actually didn't occur I'll comment because of how well things were handled. There was a last minute change that had us without a room there for the first of two nights. The manager called me the morning of our scheduled check in telling me that the hotel did not have a room for the first night. I didn't know that could happen. The manager had already found another hotel that was only 2 blocks away and set that up for us. He also comp'ed the first day. We decided to stay at the new hotel for both nights for convience. We stopped by the Kellogg to meet the manager and say thank you for handling the situation so well.

Reviewed on Apr 24, 2023

InterContinental Washington D.C. - The Wharf by IHG
5.0-star property

InterContinental Washington D.C. - The Wharf by IHG

9.4/10 Exceptional! (1,068 reviews)

May 26 - May 30

4 night stay

Chicago (ORD) to Washington (DCA)

American Airlines • Coach

Washington (DCA) to Chicago (ORD)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,423, price is now $850 per person
$850
per person
found 3 hours ago
Great hotel! Everything is new. A bit farther from national mall than

Reviewed on Apr 7, 2026

Hyatt Place Arlington/Courthouse Plaza
3.0-star property

Hyatt Place Arlington/Courthouse Plaza

9.2/10 Wonderful! (1,103 reviews)

May 15 - May 18

3 night stay

Chicago (CHI) to Washington (DCA)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $937, price is now $650 per person
$650
per person
found 11 hours ago
Clean, wonderful staff and best location

Reviewed on Dec 28, 2025

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More About Flying To Leesburg from Chicago

Route Information for Flights from Chicago to Leesburg

Origin Airport IATA Code
CHI
Destination Airport IATA Code
WAS
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Leesburg

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.