Near East Side Vacations from $556

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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 Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
$556
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (573 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$607
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
This was, by far, one of the best value-to-cost properties I've stayed with during a work trip. The rooms were clean, the complimentary breakfast was delicious, and the hotel was centrally located. Would definitely stay again!

Reviewed on Oct 1, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
Save 100% on your flight
$558
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (178 reviews)
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Save 100% on your flight
$740
per person
Dec 16 - Dec 23
just found
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
8.6/10 Excellent! (1,003 reviews)
We had such a great experience at Harrah’s Casino & Hotel! We stayed for one night to celebrate my birthday, and everything was wonderful from start to finish. Our room was nice, clean, and comfortable, and the staff was absolutely amazing—everyone we interacted with was so friendly and welcoming. The casino was a lot of fun, and we also had lunch at Cross Street Grill. The food was delicious, the prices were great, and it was such a convenient option right on site. Overall, we had an amazing birthday getaway and would definitely recommend Harrah’s to anyone looking for a fun and relaxing trip. We’re already talking about planning our next visit!

Reviewed on Sep 29, 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
Save 100% on your flight
$1,224
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.8/10 Exceptional! (1,010 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.

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.

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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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Near East Side Hotel Deals

Swissotel - Chicago

Swissotel - Chicago

323 E Wacker Dr Chicago IL
$221 nightly
$263 total
Oct 31 - Nov 1
Total with taxes and fees
9/10 Wonderful! (3,528 reviews)
"Good"

Reviewed on Oct 1, 2026

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! (2,123 reviews)
"A lot or"

Reviewed on Oct 1, 2026

Radisson Blu Aqua Hotel Chicago
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$167 nightly
$199 total
Nov 1 - Nov 2
Total with taxes and fees
River Hotel
See all 4,454 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.
All Inclusive Vacations
All Inclusive Vacations
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Kid Friendly Vacations
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Romantic Vacations
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Ski Vacations
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LGBTQ Friendly Vacations
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Adventure Vacations
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Where to go when
Where to go when
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Honeymoon Vacations
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Mountain Vacations
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Yoga Vacations
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Cheap Vacations
Solo Vacations
Solo Vacations

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.