East Side Holidays

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Price found within the past 48 hours. Click for updated prices.
Great Wolf Lodge Illinois

Great Wolf Lodge Illinois

3 out of 5
Price was €1,454, price is now €750 per person
€750
per person
1 Aug - 5 Aug
found 1 day ago
Return flight included
Phoenix (PHX) to Chicago (ORD)
8.6/10 Excellent! (1,003 reviews)
Kids had fun, it was a great stay.

Reviewed on 19 Jun 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was €1,974, price is now €1,308 per person
€1,308
per person
25 Jul - 31 Jul
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
everyone at the front desk was helpful and quite nice. room and amenities very clean. gym was well done for such a small space. would be great if there was a bathroom there. coffee and fresh fuit in the morning was awesome.

Reviewed on 19 Jun 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €2,287, price is now €1,546 per person
€1,546
per person
25 Jul - 31 Jul
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
This location is primarily a place where people live as in an apartment complex. The hotel part of it seems to be more for people doing longer stays. That means you’re not get the normal amenities or service you would get with a more traditional hotel. It is not a bad location, but I would try not to stay here again.

Reviewed on 20 Jun 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €2,371, price is now €1,622 per person
€1,622
per person
25 Jul - 31 Jul
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
Comfortable, modern rooms and great location.

Reviewed on 19 Jun 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €2,658, price is now €1,837 per person
€1,837
per person
25 Jul - 31 Jul
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,735 reviews)
Excellent hotel to stay in. Surrounded by so many things Chicago has to offer. Right across from the river. We were greeted nicely, was able to upgrade to a nicer room at a fair price. Check in was smooth. Room was very nice, well maintained hotel lobby, rooms hallways etc. had breakfast in the Land and Sea restaurant downstairs due to a rainy morning. Would definitely recommend staying at the London House for a stay in Chicago.

Reviewed on 15 Jun 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

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 €141 per night from 30 Jun to 1 Jul
€141
30 Jun - 1 Jul
includes taxes & fees
8/10 Very Good! (10,140 reviews)
"Complicated"

Reviewed on 19 Jun 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is €134 per night from 29 Jun to 30 Jun
€134
29 Jun - 30 Jun
includes taxes & fees
7.8/10 Good! (1,598 reviews)
"Our stay was amazing! Staff was very helpful!"

Reviewed on 19 Jun 2026

The Chicago Hotel Collection - Magnificent Mile
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is €160 per night from 29 Jun to 30 Jun
€160
29 Jun - 30 Jun
includes taxes & fees
8.2/10 Very Good! (1,619 reviews)
"Air conditioning not working"

Reviewed on 19 Jun 2026

The Chicago Hotel Collection Ambassador Gold Coast
See all 4,154 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 €750, 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

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

Wrigley Field
A coastal cityscape with high-rise buildings, a marina, and a park area.

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

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
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€37
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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.