East Side Holidays

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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 which includes 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

Top hotels in East Side

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is €118 per night from 1 Apr to 2 Apr
€118
1 Apr - 2 Apr
includes taxes & fees
8/10 Very Good! (9,977 reviews)
Overall, the hotel was clean, and the lounge was spacious, well-organized, and inviting. The property is a bit older, but not in a negative way—it simply has that classic feel. Our room was on the 5th floor, and the area was quiet, which made our stay very comfortable. The location is also excellent. ...

Reviewed on 21 Mar 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is €158 per night from 6 Apr to 7 Apr
€158
6 Apr - 7 Apr
includes taxes & fees
9.4/10 Exceptional! (3,577 reviews)
The breakfast was incredibly delicious. The hotel in general is a 10 out of 10.

Reviewed on 20 Mar 2026

Hotel Riu Plaza Chicago
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
Fully refundableReserve now, pay when you stay
The price is €132 per night from 29 Mar to 30 Mar
€132
29 Mar - 30 Mar
includes taxes & fees
8.6/10 Excellent! (5,757 reviews)
Hotel is conveniently located, clean and rooms were spacious. Evening reception and breakfast selections are fantastic. The only downside was the pool area is small with limited seating but the kiddos still enjoyed. Staff was very professional and helpful. Would stay again.

Reviewed on 20 Mar 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,253 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 featuring central business district, a city and a sporting event

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
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home 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(125 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

€23
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

€38
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

€34
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.