Ashburn Vacations from $258

Book a Hotel + Flight or Car together to unlock savings

Your Ashburn Vacation

Book an Ashburn vacation package and experience the rhythm and lifestyle of this fascinating neighborhood. With all your travel plans taken care of, the only thing you need to worry about here is having the time of your life. If you're all about sightseeing, no trip to Ashburn is complete without a visit to nearby Highland Community Bank. Whatever your ideal Ashburn vacation looks like, you can make it a reality with Expedia.

The Latest Ashburn Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Save 100% on your flight
Price was $424, price is now $258 per person
$258
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.6/10 Exceptional! (246 reviews)
Very clean and the staff was very friendly and helpful

Reviewed on Oct 4, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,560, price is now $638 per person
$638
per person
Dec 23 - Dec 28
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,046 reviews)
One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done.

Reviewed on Oct 2, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,229, price is now $685 per person
$685
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
Excellent location, great restaurants nearby. Nice, spacious rooms.

Reviewed on Oct 3, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,181, price is now $712 per person
$712
per person
Dec 13 - Dec 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Beautiful hotel in great walkable area. There were major renovations going on while we were there so our actual floor was a bit messy/busy, although the common areas remained lovely. Would stay again for the good location. All staff very nice.

Reviewed on Sep 29, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,474, price is now $894 per person
$894
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (698 reviews)
Great location and weight room

Reviewed on Oct 5, 2025

Where to stay in Ashburn

Find the best Ashburn areas and neighborhoods for the activities you enjoy most. Learn more about Ashburn
Downtown Chicago showing a city

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Ashburn Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $170 total per night from Nov 2 to Nov 3
$170 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (9,273 reviews)
"Rooms were updated"

Reviewed on Oct 3, 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $125 total per night from Nov 4 to Nov 5
$125 total
Nov 4 - Nov 5
Total with taxes and fees
7.8/10 Good! (2,410 reviews)
"Staff very helpful and polite"

Reviewed on Oct 2, 2025

Freehand Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
$169 nightly
The price is $199 total per night from Nov 5 to Nov 6
$199 total
Nov 5 - Nov 6
Total with taxes and fees
8.4/10 Very Good! (5,027 reviews)
"Staff was amazing. Bed was extremely comfortable. Very clean room."

Reviewed on Oct 4, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,611 properties in Ashburn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Ashburn

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

$44
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.