East Side Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to Rp16.000.000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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

4 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

Top hotels in East Side

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is Rp1.493.915 per night from 27 May to 28 May
Rp1.493.915
Rp2.301.627 total
27 May - 28 May
includes taxes & fees
8.2/10 Very Good! (2,655 reviews)
It was ok

Reviewed on 28 Apr 2026

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is Rp2.472.360 per night from 25 May to 26 May
Rp2.472.360
Rp2.939.560 total
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (5,143 reviews)
Everything was great until morning then our room filled up with smoke otherwise it was good

Reviewed on 27 Apr 2026

River Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is Rp1.887.186 per night from 25 May to 26 May
Rp1.887.186
Rp2.243.807 total
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (3,472 reviews)
Quite. Clean, Safe

Reviewed on 27 Apr 2026

Club Quarters Hotel, Central Loop, Chicago
See all 4,297 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.

Frequently asked questions

How much does an East Side holiday package cost?
Our East Side holiday packages, which start from just , are an awesome way to save precious money. Select your preferred hotels, flights and more to create your ideal escape.
How do I get a cheap travel package to East Side?
Bundle your hotels and flights with Expedia to save on your next adventure. With more than 550 air carriers and 1,000,000 properties globally, your East Side holiday package can be customized exactly to suit your budget. With all that extra money, why not throw in one or two interesting tours and experiences? It's an easy way to unlock even more bargains. That dream holiday to East Side is closer than you thought!
Where should I stay in East Side?
With popular attractions such as Calumet Beach and Calumet Park in this area, look for a hotel positioned near either one. Bronzeville Childrens Museum is another East Side sight that lures the crowds.
How far in advance should I book my East Side holiday?
Reserving your spot early with Expedia means one less thing to have to worry about. Most air carriers advertise tickets up to 12 months in advance. Typically, this is the cheapest time to book. If circumstances have left you booking late, low prices to East Side sometimes emerge just weeks before departure.
What does an Expedia East Side travel package include?
Car rentals, hotels and flights — we connect you to the very best deals. All you'll have to do is pick and choose your preferred combination. After you've made your booking, you can add on the exciting stuff like activities and tours. Our travel packages make it simple to customize an amazing East Side escape.
What should I know before booking an East Side travel package?
We already have low prices. However, you'll pick up even better deals if you book your flights, hotels and car rentals together. With an Expedia package, you'll get transparent pricing and tons of choice.
Can I choose my airline with an East Side Expedia holiday package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines globally. Our holiday packages give you the freedom to take your pick of available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my East Side holiday package?
Don't stress if you're rethinking your East Side holiday package — you can cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We realise life can occasionally throw a spanner in the travel works, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.

Popular places to visit

Wrigley Field

Wrigley Field

4.5/5(40 reviews)

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

Wrigley Field
Millennium Park

Millennium Park

4.5/5(147 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Six Flags Great America

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

Rp459.054
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

Rp703.203
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

Rp1.853.218
per adult
90% of travellers recommend
Chicago C3® by CityPASS®
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.