East Side Vacations from $273
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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 Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $447, price is now $273 per person
$273
per person
Apr 10 - Apr 13
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
Liked the neat and tidy room I was assigned to. They accommodated my request for the shower. Staff showed great hospitality special thanks to Sasha, Konnor, Rigel. Would have been greater had there been more amenities like body lotion, sleeper, toothbrush, etc.
Reviewed on Jan 7, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $597, price is now $342 per person
$342
per person
Apr 10 - Apr 13
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Cleanliness, exceptional customer service, and a complimentary upgrade made our stay outstanding! The way the buffet staff efficiently managed the line, guided guests to tables, and consistently kept the food fresh—all while wearing genuine smiles—was truly impressive. Our room was spotless, modern, and well-stocked, exceeding our expectations. We will definitely be back!
Reviewed on Jan 11, 2026
Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
Save 100% on your flight
Price was $564, price is now $348 per person
$348
per person
Apr 3 - Apr 8
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
I was greeted with a smile we checking our room and we were late. They were very accommodating. They have a bar which we went over to eat from. I don’t know the bartender’s real name we were cold to call her TT. She was the very best ever very kind very sociable and friendly. I will be returning to this property the next time I’m in Chicago. I really had a great experience at this hotel with the staff is also includes the manager the hotel clerk, as well as the security guard. I will give my experience at this hotel five stars.
Reviewed on Jan 12, 2026
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $660, price is now $413 per person
$413
per person
Apr 10 - Apr 13
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Had an amazing stay. Just note, you need to ask for the room cleaning service, and its not for everyday. Overall really loved the place and hope to come back!
Reviewed on Jan 10, 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
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $192 total per night from Jan 20 to Jan 21
$192 total
Jan 20 - Jan 21
Total with taxes and fees
8.4/10 Very Good! (2,529 reviews)
Nice size rooms, accommodating check in help, and great location
Reviewed on Jan 12, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $105 total per night from Jan 25 to Jan 26
$105 total
Jan 25 - Jan 26
Total with taxes and fees
8.8/10 Excellent! (3,708 reviews)
The staff was amazing and helpful. The room was very clean and the view was beautiful. Everything was so relaxing i hardly wanted to leave the room. I had the best sleep ever in the comfortable king size bed. The gym my great , hot towels, water and headphones to use on the equipment. I stayed for ...
Reviewed on Jan 13, 2026
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$168 nightly
The price is $193 total per night from Jan 20 to Jan 21
$193 total
Jan 20 - Jan 21
Total with taxes and fees
8.4/10 Very Good! (2,240 reviews)
Best hotel in Chicago
Reviewed on Jan 13, 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.
Discover the most popular places to visit in East Side
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
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.
Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
100% of travellers recommend
Chicago Bulls Basketball Game at United Center
$83
per adult
80% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.