Name: Freehand Chicago
Price range: $146 total

Your Uptown Vacation

Take the stress out of travel planning with an Uptown vacation package. With all the details organized before you set off, all you have to do is simply enjoy this residential neighborhood's cafes, history and culture. Not sure what to see and do during your trip to Uptown? Nearby attractions like Lincoln Park, Loyola University Chicago and Aragon Ballroom are great places to start. Expedia can help you turn your ideal Uptown vacation into reality, no matter your travel plans or budget.

The Latest Uptown Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$390

per person

Nov 14 - Nov 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.4/10 Very Good! (3,812 reviews)

The bathtub was filthy. Coffee pod from previous guest still in keureg, only one coffee cup. Headboard detached from bed unstable. Staff not very engaging.

Reviewed on Sep 11, 2025

The Emily Hotel

Downtown Chicago

$649

per person

Nov 25 - Dec 2

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (1,195 reviews)

The rooms were not very well decorated. The furniture used in the room looks like furniture from a detention house. Not my favorite.

Reviewed on Sep 8, 2025

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$473

per person

Oct 17 - Oct 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (2,373 reviews)

We were extremely impressed with the property. From the staff to the rooms to the food/drink options, everything was top notch.

Reviewed on Sep 10, 2025

Hampton Inn & Suites Chicago Medical District UIC

Near West Side

Save 100% on your flight

$522

per person

Oct 16 - Oct 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.6/10 Exceptional! (237 reviews)

New hotel with a friendly staff and clean modern rooms.

Reviewed on Sep 8, 2025

Pendry Chicago

Downtown Chicago

Save 100% on your flight

$492

per person

Oct 30 - Nov 2

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (1,070 reviews)

The property is gorgeous! Lovely rooms and the staff were fantastic, could not fault them at all! My only issue would be the roads outside are very noisy, we needed ear plugs to sleep. Other than that, absolutely fantastic stay! Would return and would highly recommend

Reviewed on Sep 8, 2025

Where to stay in Uptown

Find the best Uptown areas and neighborhoods for the activities you enjoy most. Learn more about Uptown

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.

Uptown Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Fully refundableReserve now, pay when you stay

$179 nightly

$210 total

Sep 22 - Sep 23

Total with taxes and fees

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL

$175 nightly

$206 total

Sep 22 - Sep 23

Total with taxes and fees

Freehand Chicago

19 East Ohio Street, Chicago, IL

Fully refundableReserve now, pay when you stay

$124 nightly

$146 total

Sep 24 - Sep 25

Total with taxes and fees

See all 4,496 properties in Uptown

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.