East Side Holidays

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to €185 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place
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
per person
14 May - 21 May
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8/10 Very Good! (1,524 reviews)
Love booking a room there

Reviewed on 23 Mar 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
14 May - 21 May
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,036 reviews)
The Emily Hotel is a phenomenal place. Leo at the front desk was amazing at checking us in and making our experience so much better. Great stay!! And we look forward to going back for rooftop movie nights!!!

Reviewed on 23 Mar 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
15 May - 20 May
found 3 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,310 reviews)
Great stay on St. Patrick's Day weekend.

Reviewed on 24 Mar 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
14 May - 21 May
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,546 reviews)
Excellent, just what anyone would expect from this brand.

Reviewed on 25 Mar 2025

Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
per person
15 May - 20 May
found 3 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,608 reviews)
The staff was great, it was nice they have a free cocktail bar at night where you get two adult beverages everyday. The breakfast was decent for a free breakfast. the bad, the hotel was under construction which was not communicated at time of booking. Only one elevator was operational so the wait times were long every time. The walls in the hotel were paper thin. The room next to us was empty but we could hear the kids two rooms down our entire stay. Pictures online show a walk in shower, not what our room had, and the beds were not comfortable.

Reviewed on 24 Mar 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 featuring a city

Downtown Chicago

5 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Top hotels in East Side

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 €138 per night from 13 Apr to 14 Apr
€138
includes taxes & fees
13 Apr - 14 Apr
8.2/10 Very Good! (3,756 reviews)
"This is a great property for families. It had a large breakfast area. A lot of places to hang out outside of the room. The view from the room was great too."

Reviewed on 24 Mar 2025

Embassy Suites by Hilton Chicago Downtown River North
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €107 per night from 13 Apr to 14 Apr
€107
includes taxes & fees
13 Apr - 14 Apr
8.6/10 Excellent! (3,958 reviews)
"Great stay!"

Reviewed on 24 Mar 2025

River Hotel
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is €107 per night from 30 Mar to 31 Mar
€107
includes taxes & fees
30 Mar - 31 Mar
8.6/10 Excellent! (1,025 reviews)
"They made us feel right at home and accommodated us"

Reviewed on 24 Mar 2025

Crowne Plaza Chicago West Loop by IHG
See all 3,878 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 €1,548, 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
McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Magnificent Mile - River North showing street scenes, signage and night scenes

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

Things to do

Flyover in Chicago

Flyover in Chicago

€35
per adult
96% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

€45
per adult
94% of travellers recommend
Architecture River Tour
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

€41
per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
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.