East Side Vacations from $683
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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.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,216, price is now $797 per person
$797
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,374, price is now $914 per person
$914
per person
Jul 31 - Aug 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
Breakfast was incredible. Location was great and provided easy access to the city, sights and CTA
Reviewed on Jun 26, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,422, price is now $1,033 per person
$1,033
per person
Aug 26 - Aug 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
Fantastic hotel, super clean and excellent customer service, I would recommend it to anyone going to Chicago
Reviewed on Jun 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
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.
East Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $162 total per night from Jun 29 to Jun 30
$162 total
Jun 29 - Jun 30
Total with taxes and fees
8/10 Very Good! (10,129 reviews)
"Great experience! Close to everywhere we wanted to go!"
Reviewed on Jun 26, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $166 total per night from Jul 6 to Jul 7
$166 total
Jul 6 - Jul 7
Total with taxes and fees
9/10 Wonderful! (4,461 reviews)
"Great stay. Convenient to where we wanted to go and easy access to the bus"
Reviewed on Jun 26, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$194 nightly
The price is $231 total per night from Jul 5 to Jul 6
$231 total
Jul 5 - Jul 6
Total with taxes and fees
9.4/10 Exceptional! (4,540 reviews)
"Breakfast was incredible. Location was great and provided easy access to the city, sights and CTA"
Reviewed on Jun 26, 2026
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.
Stay near popular East Side attractions
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.