Galewood Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩1,660,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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

Galewood Hotel Deals

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 ₩301,136 per night from Jun 2 to Jun 3
₩301,136
₩358,019 total
Jun 2 - Jun 3
includes taxes & fees
8/10 Very Good! (10,120 reviews)
"The Congress is old but it never fails!!! Great location!!! I have stayed there many of times …"

Reviewed on May 28, 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 ₩358,510 per night from Jun 16 to Jun 17
₩358,510
₩468,998 total
Jun 16 - Jun 17
includes taxes & fees
9.4/10 Exceptional! (4,277 reviews)
"This newer hotel was very nice. Clean efficient rooms. Great bathroom and sizable room. Hotel bar looked very cool and roof top bar good and not too crowded. However we were told that most of the roof top tables were reserved even though we arrived right when it opened and in a slower Wednesday night. ..."

Reviewed on May 28, 2026

Hotel Riu Plaza Chicago
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 ₩227,994 per night from Jun 28 to Jun 29
₩227,994
₩271,063 total
Jun 28 - Jun 29
includes taxes & fees
7.8/10 Good! (1,485 reviews)
"we ended up having to pay $90 on top of what we paid on this app for no reason, our hotel was fully paid yet they charged us this without explaining what it was for, I didn’t want to ask because I was already stressed about not being able to check in early and being late to our activities for the ..."

Reviewed on May 28, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 5,012 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 vacation package cost?
From just . Yes, you read that right. Our Galewood packages are a simple way to make your dollars go much further. Combine your favorite 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 vacation 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 vacation 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 vacation fantasies.
Where should I stay in Galewood?
Most who travel to Galewood include University of Illinois Chicago and United Center 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 vacation?
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 vacation 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. Vacationing 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 vacation package?
Yes — that's one of the best things about an Expedia vacation 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 vacation package?
Plans can change in the blink of an eye, so yes, you can. You may be able to cancel or alter your Galewood vacation 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.

Discover the most popular places to visit in Galewood

Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Millennium Park

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park

Grant Park

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.