Uptown Vacations from $495

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
Save 100% on your flight
$495
per person
Oct 21 - Oct 25
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,879 reviews)
Gym was awesome. First time in Chicago. This was a great place to stay: wish there was more of a bar scene / restaurant but still great.

Reviewed on Aug 10, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
$768
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
Great staff, great place!

Reviewed on Aug 5, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
$2,857
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The

Reviewed on Aug 10, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$696
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Breakfast lovely, with a lot of options that varied daily. I love the Riu hotels, and this one didn’t disappoint. Would definitely return.

Reviewed on Aug 10, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
$900
per person
Oct 21 - Oct 25
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
We were in town for a family event. Had three rooms because of adult children. Everyone was friendly and helpful. Nice quiet location in downtown. Highly recommend.

Reviewed on Aug 10, 2026

Where to stay in Uptown

Find the best Uptown areas and neighborhoods for the activities you enjoy most. Learn more about Uptown
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 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
A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

Find hotels in The Loop
A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

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A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

Find hotels in River North
A nighttime cityscape with fireworks over a body of water, a Ferris wheel, and illuminated buildings.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).

Find hotels in Theatre District

Uptown Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$117 nightly
$140 total
Sep 8 - Sep 9
Total with taxes and fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$143 nightly
$170 total
Aug 30 - Aug 31
Total with taxes and fees
8/10 Very Good! (1,976 reviews)
"Great location for our stay, but the "double" beds seemed even tinier than doubles, the bathrooms are old and could use a refresh- drainage in the shower was an issue, and they wouldn't refresh the room in the middle of a 4 day stay- just dropped off new sheets and towels. Lobby is nice, and the ..."

Reviewed on Aug 10, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
$226 nightly
$265 total
Sep 5 - Sep 6
Total with taxes and fees
Hilton Chicago O'Hare Airport
See all 4,513 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.
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Stay near popular Uptown attractions

A historic theater with ornate architecture and a prominent marquee.

Aragon Ballroom

9.2/10 (10 reviews)
Catch an event at Aragon Ballroom during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
See properties
A frozen river with a city skyline in the background.

Montrose Beach

Soak up the sun with views of Lincoln Park and Lake Michigan at this city beach known for its fun sports and extensive amenities.
See properties
A marina with various sailboats and yachts docked.

Montrose Harbor

With trails, a beach and a bird sanctuary, this spacious city harbor is a good place to sail from and a great place to hang out.
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A city street with a bus stop, trees, and buildings.

Hutchinson Street Historic District

You can learn about the history of Chicago when you stop by Hutchinson Street Historic District. Experience the acclaimed art scene and entertainment choices in this vibrant area.
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Riviera Theatre

8.0/10 (1 review)
You can enjoy a show at Riviera Theatre during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
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Pegasus Players

You can get tickets for a performance at Pegasus Players during your trip to Chicago. Experience the acclaimed art scene and entertainment choices in this vibrant area.
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Aragon Entertainment Center

6.0/10 (1 review)
You can enjoy a show at Aragon Entertainment Center on your trip to Chicago. Experience the entertainment choices and acclaimed art scene in this vibrant area.
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Black Ensemble Theater

You can make plans for a show at Black Ensemble Theater on your trip to Chicago. Experience the area's theater scene and live music.
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$27
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

$47
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
90% 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.