East Side Vacations from $266

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Your East Side Vacation

Book a vacation package to East Side and experience the wonders of this neighborhood from dawn to dusk. From its nature and walking to its unique rhythm and vibe, there's an endless list of great reasons to visit East Side. Start your trip to East Side by checking out nearby attractions such as Calumet Park, Calumet Beach and Munson Beach. Don't just wish for it — make it a reality! Lock in your ultimate East Side vacation with Expedia and experience travel your way.

The Latest East Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $500, price is now $266 per person
$266
per person
May 8 - May 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great staff, clean rooms. Great location

Reviewed on Feb 21, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $863, price is now $501 per person
$501
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Had a great stay!! Kelly at the front desk was so sweet

Reviewed on Feb 22, 2026

Holiday Inn Club Vacations at Lake Geneva Resort by IHG

Holiday Inn Club Vacations at Lake Geneva Resort by IHG

3.5 out of 5
Price was $570, price is now $336 per person
$336
per person
May 2 - May 7
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
8.8/10 Excellent! (1,003 reviews)
Clean room. The only bad thing was that the Grand Geneva Hotel makes sure to let you know that they are only there to check you in nothing else. We were there for three nights, and nobody ever came to take garbage or anything.

Reviewed on Feb 19, 2026

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $666, price is now $401 per person
$401
per person
May 1 - May 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
The room was great and clean , there was a toilet issue but the staff members gladly were readily available to fix it all ! The amenities including the hot tub, and pool as well as the in room service breakfast was 5/5 . Would absolutely stay here again .

Reviewed on Feb 17, 2026

La Banque Hotel

La Banque Hotel

4 out of 5
Price was $934, price is now $575 per person
$575
per person
May 1 - May 6
found 3 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

Where to stay in East Side

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

East Side Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $109 total per night from Feb 23 to Feb 24
$109 total
Feb 23 - Feb 24
Total with taxes and fees
8/10 Very Good! (9,925 reviews)
Room was very cold, key didn’t work for the side door

Reviewed on Feb 22, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $144 total per night from Mar 4 to Mar 5
$144 total
Mar 4 - Mar 5
Total with taxes and fees
9.4/10 Exceptional! (3,385 reviews)
Great staff, clean rooms. Great location

Reviewed on Feb 21, 2026

Hotel Riu Plaza 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
$98 nightly
The price is $116 total per night from Mar 4 to Mar 5
$116 total
Mar 4 - Mar 5
Total with taxes and fees
8.6/10 Excellent! (5,683 reviews)
The staff were friendly, the room was clean, and this hotel is in a great location. We were able to walk to a lot of attractions. My main issue with this hotel is that it was too popular! It was really crowded when we were there and even with 4 elevators sometimes there was a wait. Still, I would ...

Reviewed on Feb 21, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,303 properties in 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 East Side

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
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

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
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

Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$166
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Picture 7 for Activity Chicago River: 1.5-Hour Guided Architecture Cruise

Chicago River: 1.5-Hour Guided Architecture Cruise

$44
per adult
98% of travellers recommend
Chicago River: 1.5-Hour Guided Architecture Cruise
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.