Near East Side Vacations from $274

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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.
Holiday Inn Express & Suites Zion by IHG

Holiday Inn Express & Suites Zion by IHG

2.5 out of 5
Save 100% on your flight
Price was $392, price is now $274 per person
$274
per person
Apr 23 - Apr 27
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (186 reviews)
Staff was Excellent! Room was super clean!

Reviewed on Feb 20, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,409, price is now $862 per person
$862
per person
May 26 - May 30
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Interesting property in that it is a high rise building of furnished suites with certain floors available as a “hotel”. Coffee shop, gym and lounge are all nice as are the suites. Just know this is not a service oriented hotel experience. No doorman, uniformed person at desk, room or maid service etc.

Reviewed on Mar 14, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $628, price is now $385 per person
$385
per person
Apr 30 - May 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Great stay! No complaints! Breakfast buffet was a great plus!

Reviewed on Mar 15, 2026

Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Save 100% on your flight
Price was $805, price is now $532 per person
$532
per person
May 23 - May 30
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
8/10 Very Good! (503 reviews)
Pool was out of commission. Front desk was welcoming.

Reviewed on Mar 5, 2026

Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
East Hazel Crest
Save 100% on your flight
Price was $796, price is now $561 per person
$561
per person
May 21 - May 24
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (MDW)
9.4/10 Exceptional! (278 reviews)
The room was very clean but the lighting in the room is very dark.

Reviewed on Mar 2, 2026

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
Downtown Chicago showing a city

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.

Find hotels in Downtown Chicago

Near East Side Hotel Deals

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
323 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $178 total per night from Mar 29 to Mar 30
$178 total
Mar 29 - Mar 30
Total with taxes and fees
9/10 Wonderful! (3,228 reviews)
Prefect location in the city by the river

Reviewed on Mar 16, 2026

Swissotel - Chicago
Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
221 N Columbus Dr Chicago IL
Fully refundableReserve now, pay when you stay
$170 nightly
The price is $200 total per night from Mar 29 to Mar 30
$200 total
Mar 29 - Mar 30
Total with taxes and fees
8.6/10 Excellent! (1,870 reviews)
Clean rooms, friendly staff

Reviewed on Mar 15, 2026

Radisson Blu Aqua Hotel Chicago
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $124 total per night from Apr 1 to Apr 2
$124 total
Apr 1 - Apr 2
Total with taxes and fees
8/10 Very Good! (9,944 reviews)
Very cool place to stay if you enjoy historic buildings. I would definitely stay here again. Clean room, walking distance to many places.

Reviewed on Mar 16, 2026

Congress Plaza Hotel
See all 4,622 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
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Near East Side

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$26
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

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