Near East Side Vacations from $299

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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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $558, price is now $299 per person
$299
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.

Reviewed on Dec 8, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,178, price is now $538 per person
$538
per person
Jan 14 - Jan 18
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.8/10 Excellent! (1,075 reviews)
We love it there! The best

Reviewed on Nov 30, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $638, price is now $358 per person
$358
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
The rooms were great. Very spacious, fully stocked kitchen and extremely clean. We loved having access to the 8th floor with the steam room, sauna, fitness center, game rooms, and socializing areas 24/7. Would love to experience it in the summer with the pool and outdoor areas. We were also fortunate enough to attend during their Christmas Brunch buffet which was such a great perk! If the price stays around the same, I will continue to stay at Level hotels exclusively in any cities I visit that has one! I’ve already told so many people about my wonderful hotel experience.

Reviewed on Dec 9, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,081, price is now $610 per person
$610
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
All of the above. Staff was wonderful. Room was clean and comfortable. On site amenities were great and food was superb. Best espresso martini I’ve ever tasted.

Reviewed on Dec 11, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $745, price is now $427 per person
$427
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
The room was beautiful and clean and a good city view of the city

Reviewed on Nov 26, 2025

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
$139 nightly
The price is $163 total per night from Jan 1 to Jan 2
$163 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.8/10 Excellent! (3,004 reviews)
The view from the room was nice. Loved the gym and amenities. A decent place to stay. The best part of the visit was the Palm restaurant (great food and service).

Reviewed on Dec 11, 2025

Swissotel - Chicago
Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
221 N Columbus Dr Chicago IL
Fully refundable
$162 nightly
The price is $190 total per night from Dec 28 to Dec 29
$190 total
Dec 28 - Dec 29
Total with taxes and fees
8.4/10 Very Good! (1,789 reviews)
Balcony was greatly appreciated

Reviewed on Dec 8, 2025

Radisson Blu Aqua Hotel Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $113 total per night from Jan 6 to Jan 7
$113 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
8.4/10 Very Good! (5,379 reviews)
The stay was fantastic and the room was very spacious.

Reviewed on Dec 12, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,668 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

Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

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
Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

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

Wrigley Field
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

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

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

$44
per adult
96% of travellers recommend
Architecture River Tour
Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$80
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
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.