Galewood Holidays

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Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Downtown Chicago
Price was €1,693, price is now €1,349 per person
€1,349
per person
23 Jun - 30 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (5,808 reviews)
Great location, great staff, great rooms!

Reviewed on 12 Apr 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €3,471, price is now €2,546 per person
€2,546
per person
24 Jun - 30 Jun
found 1 day ago
Return direct flight included
Johannesburg (JNB) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!

Reviewed on 7 Apr 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was €2,476, price is now €1,860 per person
€1,860
per person
24 Jun - 30 Jun
found 1 day ago
Return direct flight included
Johannesburg (JNB) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Overall we enjoyed our stay. A few things that we didn’t care for. One is that the parking was inconvenient due to you having to call to get in every time you leave. Next would be the closet with the furnace was extremely noisy and almost kinda sounding. It came off and on very frequently. Lastly, the bed was as hard as a rock. If you are used a nice bed you can forget it. For the price no thx.

Reviewed on 12 Apr 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was €2,396, price is now €1,889 per person
€1,889
per person
24 Jun - 30 Jun
found 1 day ago
Return direct flight included
Johannesburg (JNB) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Very friendly staff, great location.

Reviewed on 6 Apr 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was €2,130, price is now €1,701 per person
€1,701
per person
24 Jun - 30 Jun
found 1 day ago
Return direct flight included
Johannesburg (JNB) to Chicago (ORD)
8.2/10 Very Good! (2,604 reviews)
Nice, but no microwave or refrigerator in room. Staff is nice and place was clean. Many things to do around.

Reviewed on 11 Apr 2026

Where to stay in Galewood

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

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 €123 per night from 26 Apr to 27 Apr
€123
26 Apr - 27 Apr
includes taxes & fees
8/10 Very Good! (10,115 reviews)
Parking was $62 per day. Hotel smelled like marijuana and there were people just outside the doors smoking. Made for a very unpleasant stay.

Reviewed on 12 Apr 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is €137 per night from 26 Apr to 27 Apr
€137
26 Apr - 27 Apr
includes taxes & fees
9/10 Wonderful! (4,118 reviews)
Great room

Reviewed on 12 Apr 2026

Hilton Chicago/Magnificent Mile Suites
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 €155 per night from 27 Apr to 28 Apr
€155
27 Apr - 28 Apr
includes taxes & fees
8.6/10 Excellent! (5,847 reviews)
Great location, great staff, great rooms!

Reviewed on 12 Apr 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 5,053 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 €1,349. 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

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
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

5/5(1 review)

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

4/5(127 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
88% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

€35
per adult
94% of travellers recommend
Art Institute of Chicago
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 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.