Galewood Holidays

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Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was €1,443, price is now €873 per person
€873
per person
4 Oct - 10 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Great location and room was fantastic! Only negatives were a lengthy check in and access to the outside deck was closed at 10 PM. Probably a good idea for that, but it would’ve been nice to go out there for a nightcap.

Reviewed on 26 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €2,460, price is now €1,429 per person
€1,429
per person
4 Oct - 10 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on 25 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €2,024, price is now €1,204 per person
€1,204
per person
2 Nov - 9 Nov
found 1 day ago
Return direct flight included
Faro (FAO) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 Aug 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €1,794, price is now €1,081 per person
€1,081
per person
4 Oct - 10 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.

Reviewed on 26 Aug 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was €1,722, price is now €1,066 per person
€1,066
per person
4 Oct - 10 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (666 reviews)
The hotel never got cool, hot everywhere, even the community areas. We had to use the TV in the communal area as ours didn't work. We called on day one and the girl laughed and never sent anyone to fix it. Our key cards didn't work multiple times during the stay. The party that happened at the pool on Sunday night of our stay was awful. I couldn't imagine what my kids saw even those this hotel said no parties.

Reviewed on 25 Aug 2025

Where to stay in Galewood

Find the best Galewood areas and neighborhoods for the activities you enjoy most. Learn more about Galewood
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 Galewood

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €168 per night from 22 Sept to 23 Sept
€168
22 Sept - 23 Sept
includes taxes & fees
The Wade
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 €199 per night from 15 Sept to 16 Sept
€199
15 Sept - 16 Sept
includes taxes & fees
7.8/10 Good! (9,022 reviews)
"Very good location"

Reviewed on 25 Aug 2025

Congress Plaza Hotel
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 €153 per night from 3 Sept to 4 Sept
€153
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,776 reviews)
"Great location, great price. Overall excellent hotel."

Reviewed on 25 Aug 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,975 properties in Galewood
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 a Galewood holiday package cost?
From just €873. Yes, you read that right. Our Galewood packages are a simple way to make your dollars go much further. Combine your favourite hotels, flights and rental car and get out and explore this wonderful destination.
How do I get a cheap travel package to Galewood?
One word: bundle. Flights, hotels and rental cars — combine whatever you need into a Galewood holiday package to save loads of cash. Score even better deals when you add extras such as activities or tours to your booking. But that's not the only impressive part. You have the freedom to put together your holiday your own way. We offer more than 550 airlines and 1,000,000 properties throughout the world, so that everyone has an opportunity to travel and live out those holiday fantasies.
Where should I stay in Galewood?
Most who travel to Galewood include University of Illinois Chicago and United Centre on their sightseeing itineraries. Why not reserve a hotel as close as possible to these main attractions?
How far in advance should I book my Galewood holiday?
It's always wise to book early. Air carriers usually advertise flight tickets around a year ahead of departure, and this is when you can land some rock-bottom prices. Just been told you should take some holiday time next week? That's alright! Expedia are never short of fantastic deals to send you on the getaway of your dreams, at an affordable price.
What does an Expedia Galewood travel package include?
From hotels and flights to rental cars, Expedia can help you shape a Galewood package that's ideal for you. Holidaying for a week or longer? Consider a flight, rental car and hotel bundle. If you can only squeeze in a quick getaway, an airfare and hotel deal may be more your style. Activities can also be added after you've booked. Our travel packages make it a breeze to save and plan.
What should I know before booking a Galewood travel package?
Our prices are already low. However, you'll snap up even more bargains when you book your hotels, flights and car rentals together. With an Expedia travel package, you'll always get transparent pricing and tons of choice.
Can I choose my airline with a Galewood Expedia holiday package?
Yes — that's one of the best things about an Expedia holiday package. You get to choose. We have more than 550 airline partners across the globe, so you have loads of choice when putting together your Galewood adventure.
If I'm not able to travel, can I cancel my Galewood holiday package?
Plans can change in the blink of an eye, so yes, you can. You may be able to cancel or alter your Galewood holiday package for free if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel and rebook, but your car rental company, airline or hotel may impose a fee. Looking for more information? Check out our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.

Popular places to visit

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

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

Wrigley Field
Magnificent Mile - River North showing street scenes, signage and night scenes

Michigan Avenue

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

Navy Pier

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

€36
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

€35
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

€39
per adult
96% of travellers recommend
Chicago By Night River & 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.