$65 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.

Sun, Jan 11 - Mon, Jan 12
MDW
Midway Intl.
IAD
Washington Dulles Intl.
$240 Roundtrip, found 4 days ago
$240
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, Jan 11 from Midway Intl. to Washington Dulles Intl., returning Mon, Jan 12, priced at $240 found 4 days ago
Sun, Jan 11 - Mon, Jan 12
ORD
O'Hare Intl.
IAD
Washington Dulles Intl.
$240 Roundtrip, found 4 days ago
$240
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, Jan 11 from O'Hare Intl. to Washington Dulles Intl., returning Mon, Jan 12, priced at $240 found 4 days ago
Sun, Jan 11 - Wed, Jan 21
ORD
O'Hare Intl.
DCA
Ronald Reagan Washington National
$423 Roundtrip, just found
$423
Roundtrip
just found
Select JetBlue Airways flight, departing Sun, Jan 11 from O'Hare Intl. to Ronald Reagan Washington National, returning Wed, Jan 21, priced at $423 just found
Sun, Jan 11 - Mon, Jan 12
RFD
Greater Rockford
DCA
Ronald Reagan Washington National
$626 Roundtrip, found 4 days ago
$626
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sun, Jan 11 from Greater Rockford to Ronald Reagan Washington National, returning Mon, Jan 12, priced at $626 found 4 days ago

Airfares from $65 One Way, $129 Round Trip from Chicago to Leesburg

Prices starting at $129 for return flights and $65 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.

Thu, Mar 5 - Mon, Mar 9
ORD
Chicago
DCA
Washington
$129 Roundtrip, found 1 day ago
$129
Roundtrip
found 1 day ago
Select United flight, departing Thu, Mar 5 from Chicago to Washington, returning Mon, Mar 9, priced at $129 found 1 day ago
Tue, Feb 3 - Wed, Feb 4
ORD
Chicago
DCA
Washington
$132 Roundtrip, found 23 hours ago
$132
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Tue, Feb 3 from Chicago to Washington, returning Wed, Feb 4, priced at $132 found 23 hours ago
Tue, Feb 10 - Wed, Feb 11
ORD
Chicago
IAD
Washington
$132 Roundtrip, found 9 hours ago
$132
Roundtrip
found 9 hours ago
Select United flight, departing Tue, Feb 10 from Chicago to Washington, returning Wed, Feb 11, priced at $132 found 9 hours ago
Thu, Jan 22 - Sat, Jan 31
ORD
Chicago
IAD
Washington
$136 Roundtrip, found 18 hours ago
$136
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Thu, Jan 22 from Chicago to Washington, returning Sat, Jan 31, priced at $136 found 18 hours ago
Thu, Jan 22 - Thu, Jan 29
MDW
Chicago
IAD
Washington
$144 Roundtrip, found 19 hours ago
$144
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Thu, Jan 22 from Chicago to Washington, returning Thu, Jan 29, priced at $144 found 19 hours ago

Leesburg economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Churchill Hotel near Embassy Row
4.0-star property

The Churchill Hotel near Embassy Row

8.8/10 Excellent! (1,915 reviews)

Feb 12 - Feb 16

4 night stay

Chicago (CHI) to Washington (DCA)

Frontier Airlines • Coach

Washington (DCA) to Chicago (CHI)

Southwest Airlines • Coach
Save 100% on your flight
Price was $484, price is now $332 per person
$332
per person
found 10 hours ago
Super attentive and hospitable staff. No free parking in the area so plan ahead. Walkable to the metro and entertainment.

Reviewed on Oct 4, 2025

Kellogg Conference Hotel at Gallaudet University
3.0-star property

Kellogg Conference Hotel at Gallaudet University

8.2/10 Very Good! (1,002 reviews)

Feb 12 - Feb 16

4 night stay

Chicago (CHI) to Washington (DCA)

Frontier Airlines • Coach

Washington (DCA) to Chicago (CHI)

Southwest Airlines • Coach
Save 100% on your flight
Price was $827, price is now $477 per person
$477
per person
found 10 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

Sofitel Washington DC Lafayette Square
5.0-star property

Sofitel Washington DC Lafayette Square

9/10 Wonderful! (1,084 reviews)

Feb 15 - Feb 18

3 night stay

Chicago (CHI) to Washington (DCA)

American Airlines • Non-stop • Coach

Washington (DCA) to Chicago (CHI)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $633, price is now $410 per person
$410
per person
found 1 day ago
Hotel was decent but was definitely not a 5 star hotel.upon arrival no door man around to help with luggage. In fact throughout our 3 day stay there was never any staff at the front entry way! We had 4 outlets all near the bed that didn’t work. They sent someone to check it out immediately but they were never fixed. Food was decent and location excellent for seeing all the attractions in DC.

Reviewed on Sep 23, 2025

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Leesburg first class flight packages

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Washington, DC/Foggy Bottom
3.0-star property

Courtyard by Marriott Washington, DC/Foggy Bottom

9/10 Wonderful! (1,000 reviews)

Feb 14 - Feb 16

2 night stay

Chicago (CHI) to Washington (DCA)

American Airlines • Roundtrip • FirstClass
Price was $559, price is now $522 per person
$522
per person
found 12 hours ago
The staff were exceptional. We left an item in the hotel when we left, and the staff were very helpful in getting this returned to us.

Reviewed on Oct 3, 2025

The Dupont Circle Hotel
4.5-star property

The Dupont Circle Hotel

9.4/10 Exceptional! (1,788 reviews)

Feb 14 - Feb 16

2 night stay

Chicago (CHI) to Washington (DCA)

American Airlines • Roundtrip • FirstClass
Price was $643, price is now $556 per person
$556
per person
found 12 hours ago
Nice hotel overall, good dining options within blocks of the hotel and conveniently close to the metro. Would recommend.

Reviewed on Oct 3, 2025

Washington Marriott at Metro Center
3.5-star property

Washington Marriott at Metro Center

9/10 Wonderful! (1,000 reviews)

Feb 14 - Feb 16

2 night stay

Chicago (CHI) to Washington (IAD)

American Airlines • Roundtrip • FirstClass
Price was $607, price is now $576 per person
$576
per person
found 12 hours ago
Friendly helpful staff. Always a smile and eye contact. Nice pool.

Reviewed on Nov 24, 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.