East Side Vacations from $326

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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.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $489, price is now $326 per person
$326
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (2,208 reviews)
Very cute decor and kind and helpful staff. Awesome location to theater and easy walk to may other places in the city.

Reviewed on Jan 27, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $746, price is now $439 per person
$439
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great breakfast buffet, incredible staff, very clean, close to everything we wanted to do! 10/10 and will certainly stay here again!

Reviewed on Jan 26, 2026

La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $787, price is now $480 per person
$480
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $658, price is now $442 per person
$442
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Property was clean, welcoming, pet friendly

Reviewed on Jan 18, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $647, price is now $441 per person
$441
per person
Mar 11 - Mar 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (766 reviews)
Great stay. Would come again.

Reviewed on Jan 19, 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
$89 nightly
The price is $104 total per night from Jan 31 to Feb 1
$104 total
Jan 31 - Feb 1
Total with taxes and fees
8/10 Very Good! (9,832 reviews)
Yes perfectly clean

Reviewed on Jan 24, 2026

Congress Plaza Hotel
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
$106 nightly
The price is $124 total per night from Feb 5 to Feb 6
$124 total
Feb 5 - Feb 6
Total with taxes and fees
8.4/10 Very Good! (5,616 reviews)
The room was clean. The staff was courteous! The breakfast was ok, the parking is charged extra-absolutely worth it!

Reviewed on Jan 26, 2026

Embassy Suites by Hilton Chicago Downtown River North
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
$133 nightly
The price is $156 total per night from Feb 11 to Feb 12
$156 total
Feb 11 - Feb 12
Total with taxes and fees
9.2/10 Wonderful! (3,243 reviews)
It was great!

Reviewed on Jan 25, 2026

Hotel Riu Plaza Chicago
See all 4,349 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

$61
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

$40
per adult
92% of travellers recommend
Art Institute of 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.