Uptown Vacations from $406

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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.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
Save 100% on your flight
$406
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,881 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$424
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
$421
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
The Emily Hotel

The Emily Hotel

Downtown Chicago
Save 100% on your flight
$409
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,347 reviews)
Well located with everything you need including bars and restaurants nearby. Right opposite the google office. It has a nice restaurant and bar downstairs and a couple of restaurants attached, including an omakase sushi restaurant which we went to - was amazing. Rooms are nice and spacious, very modern, although bathroom amenities are pretty light. Otherwise the room has everything you need including hairdryer, steamer, robes etc. hallway carpets definitely need changing but that’s being very particular. The passing trains are quite loud but they don’t run at night so sleep was uninterrupted. I would happily stay there again.

Reviewed on Oct 22, 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
Save 100% on your flight
$570
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
Amazing hotel ! Would def stay again

Reviewed on Oct 23, 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 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.

Find hotels in Magnificent Mile
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.

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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 wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

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Uptown Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$108 nightly
$129 total
Nov 10 - Nov 11
Total with taxes and fees
8/10 Very Good! (10,096 reviews)
"The hotel itself is huge with the historic main room being spectacular. Our room was a hike to get to but very clean, newer vinyl flooring, newer paint. We needed a one night stay for an event further south in the city so it was perfect for that. The location is pretty wonderful with Buckingham fountain ..."

Reviewed on Oct 24, 2026

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
$121 nightly
$143 total
Nov 22 - Nov 23
Total with taxes and fees
8/10 Very Good! (2,566 reviews)
"n/a"

Reviewed on Oct 24, 2026

The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
$138 total
Nov 22 - Nov 23
Total with taxes and fees
River Hotel
See all 4,697 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 theater 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.
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A marina with multiple sailboats docked, calm water, and a few ducks swimming.

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 row of red brick buildings with large windows, surrounded by green trees and a sidewalk.
Photo by TM

Hutchinson Street Historic District

You can learn about the history of Chicago when you stop by Hutchinson Street Historic District. Experience the entertainment choices and acclaimed art scene 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 theater scene.
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Carol's Pub

Carol's Pub is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the area's theater scene and live music.
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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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Our Lady of Lourdes Church

Our Lady of Lourdes Church is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the acclaimed theater scene and entertainment choices in this vibrant area.
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$24
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

$158
per adult
80% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
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.