Near East Side Vacations from $547

Book a Hotel + Flight or Car together to unlock savings

Photo by Deano

Your Near East Side Vacation

Lock in a vacation package to Near East Side and get set to experience its nature, walking and views. However you're planning to spend your getaway in this lakeside neighborhood, there's no shortage of opportunities for both relaxation and adventure. Can't wait to sightsee during your trip to Near East Side? Make sure you check out nearby attractions such as Millennium Park, Willis Tower and Art Institute of Chicago. No matter your travel plans or budget, booking a perfect Near East Side vacation has never been easier with Expedia.

The Latest Near East Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
Save 100% on your flight
$547
per person
Dec 19 - Dec 22
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (532 reviews)
I had booked an Executive Room months in advanced and when I got there they gave me a much smaller room then I was expecting

Reviewed on Oct 4, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$782
per person
Nov 12 - Nov 16
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
$1,076
per person
Nov 12 - Nov 16
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
$667
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (576 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
Save 100% on your flight
$585
per person
Nov 13 - Nov 16
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)

Where to stay in Near East Side

Find the best Near East Side areas and neighborhoods for the activities you enjoy most. Learn more about Near East Side
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.

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.

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.

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.

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.

Near East Side Hotel Deals

Swissotel - Chicago

Swissotel - Chicago

323 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
$221 nightly
$263 total
Oct 31 - Nov 1
Total with taxes and fees
Swissotel - Chicago
Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

221 N Columbus Dr Chicago IL
Fully refundableReserve now, pay when you stay
$245 nightly
$291 total
Oct 31 - Nov 1
Total with taxes and fees
8.6/10 Excellent! (2,138 reviews)
"I’m not opposed to pet friendly hotels but I don’t think they can accommodate allergies to dogs by having house keeping do a normal cleaning. My daughter instantly had swollen itchy eyes, coughing all night and I assumed it was a pet free room but they don’t have that. They just clean it. We left ..."

Reviewed on Oct 5, 2026

Radisson Blu Aqua Hotel Chicago
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$107 nightly
$127 total
Nov 2 - Nov 3
Total with taxes and fees
Congress Plaza Hotel
See all 4,495 properties in Near East Side
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.

Stay near popular Near East Side attractions

Swissotel Chicago

After visiting Swissotel Chicago, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or visit the notable monuments in this vibrant area.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$24
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Flyover in Chicago

Flyover in Chicago

$38
per adult
98% of travellers recommend
Flyover in Chicago
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
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.