East Side Vacations from $179

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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

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $306, price is now $179 per person
$179
per person
Jan 7 - Jan 11
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,273 reviews)
We enjoyed our stay here! There was no coffee maker in our room but instead a microwave which was odd. The facilities are nice. The building is old but still in great condition. The water has a smell to it so we had to keep refilling our water in the lobby to drink which was a bit annoying but the beds are comfy and the bathrooms decent!!

Reviewed on Oct 15, 2025

Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
Price was $985, price is now $454 per person
$454
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
10/10 Exceptional! (2 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $694, price is now $364 per person
$364
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Staff was amazing very help

Reviewed on Oct 17, 2025

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,287, price is now $769 per person
$769
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
This is a very nice hotel. The staff is super accommodating. The location is one of the best in the area for shopping and dining.

Reviewed on Oct 14, 2025

Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Price was $362, price is now $218 per person
$218
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Houston (HOU) to Chicago (ORD)
8/10 Very Good! (452 reviews)
Great location, next to the beach and parkland everywhere else. Initially, booked me into a room that had not been cleaned! Otherwise nice room. You cannot beat the location anywhere north of Chicago.

Reviewed on Oct 18, 2025

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
$145 nightly
The price is $170 total per night from Nov 2 to Nov 3
$170 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (9,473 reviews)
"Everything was great."

Reviewed on Oct 19, 2025

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
$113 nightly
The price is $133 total per night from Nov 16 to Nov 17
$133 total
Nov 16 - Nov 17
Total with taxes and fees
8.8/10 Excellent! (3,133 reviews)
"Every think was wonderful except the heater wasn’t working and the toilet was loose."

Reviewed on Oct 19, 2025

Hilton Chicago/Magnificent Mile Suites
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $100 total per night from Nov 10 to Nov 11
$100 total
Nov 10 - Nov 11
Total with taxes and fees
7.8/10 Good! (2,494 reviews)
"Bathroom recently redone and was fabulous, but room was old and tattered. Bed was nice and comfy. Nice crisp sheets."

Reviewed on Oct 18, 2025

Freehand Chicago
See all 4,124 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
Magnificent Mile - River North showing night scenes, a city and signage

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

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

$44
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

$45
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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.