East Side Vacations from $276

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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.
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Save 100% on your flight
Price was $437, price is now $276 per person
$276
per person
May 19 - May 23
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8/10 Very Good! (508 reviews)
The room was perfect but there was NO hot water

Reviewed on Apr 13, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $852, price is now $443 per person
$443
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
Hotel staff were superior! Everyone is so nice and helpful. Rooms were nice and clean, and getting my luggage up to my room was hands free thanks to the staff. Rooftop was wonderful!! Parking was easy and close, also in a great location of Downtown Chicago

Reviewed on Apr 14, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $1,613, price is now $917 per person
$917
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
This property never disappoints! The staff are awesome, particularly Nu at the front desk! Always very pleasant and friendly, provides awesome service every time we visit!

Reviewed on Apr 13, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,688, price is now $1,007 per person
$1,007
per person
May 29 - Jun 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Breakfast and parking not included

Reviewed on Apr 12, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,285, price is now $817 per person
$817
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,357 reviews)
Clean and comfortable

Reviewed on Apr 14, 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

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
$116 nightly
The price is $137 total per night from Apr 26 to Apr 27
$137 total
Apr 26 - Apr 27
Total with taxes and fees
8/10 Very Good! (10,146 reviews)
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Reviewed on Apr 14, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $140 total per night from Apr 26 to Apr 27
$140 total
Apr 26 - Apr 27
Total with taxes and fees
9/10 Wonderful! (4,123 reviews)
Great location.

Reviewed on Apr 14, 2026

Hilton Chicago/Magnificent Mile Suites
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
$139 nightly
The price is $163 total per night from Apr 26 to Apr 27
$163 total
Apr 26 - Apr 27
Total with taxes and fees
8.6/10 Excellent! (5,838 reviews)
The sheets were dirty and in the lobby it was dog poop

Reviewed on Apr 14, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,300 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

Wrigley Field

4.5/5(2,149 reviews)

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(461 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(4,925 reviews)

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

$27
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
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.