Galewood Holidays

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to NZ$2,400 when you book a flight and hotel together*

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

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Our guide on 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

Our pick of the best 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 NZ$287 per night from 29 June to 30 June
NZ$287
29 June - 30 June
includes taxes & fees
8/10 Very good! (10,189 reviews)
"I liked the property and level of personnel. Two days I attempted to eat in their, in person restaurant and was given unrealistic wait times. 45 minutes and still didn't receive food after an hour and a half. I canceled the order and was late to my event. Also there is no on-site parking. The website ..."

Reviewed on 25 June 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 NZ$337 per night from 6 July to 7 July
NZ$337
6 July - 7 July
includes taxes & fees
9/10 Wonderful! (4,457 reviews)
"The staff especially the bell hops were very helpful and friendly."

Reviewed on 25 June 2026

Hilton Chicago/Magnificent Mile Suites
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 NZ$427 per night from 5 July to 6 July
NZ$427
5 July - 6 July
includes taxes & fees
9.4/10 Exceptional! (4,531 reviews)
"The staff was wonderful. The room was beautiful. I really enjoyed myself."

Reviewed on 25 June 2026

Hotel Riu Plaza Chicago
See all 4,967 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 . 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.

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$41
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

NZ$68
per adult
92% of travellers recommend
Art Institute of Chicago
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

NZ$78
per adult
100% of travellers recommend
Chicago Sightseeing River and 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.