Galewood Vacations from NT$14,924

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    Save up to NT$5,067 when you book a flight and hotel together*

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The Latest Galewood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was NT$19,060, price is now NT$14,924 per person
NT$14,924
per person
Mar 14 - Mar 16
found 10 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
Clean room, amazinggggg views, everyone was so nice. Must go downstairs to Toro and get a martini from John!!

Reviewed on 2026/1/10

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$24,044, price is now NT$15,371 per person
NT$15,371
per person
Mar 14 - Mar 16
found 10 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Very helpful & charming staff!

Reviewed on 2026/1/18

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$29,173, price is now NT$20,166 per person
NT$20,166
per person
Mar 14 - Mar 16
found 10 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing

Reviewed on 2026/1/13

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Price was NT$30,470, price is now NT$23,002 per person
NT$23,002
per person
Mar 14 - Mar 16
found 10 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return.

Reviewed on 2026/1/5

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was NT$20,371, price is now NT$15,936 per person
NT$15,936
per person
Mar 14 - Mar 16
found 10 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
no the room was dirty and smell musty

Reviewed on 2026/1/18

Where to stay in Galewood

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

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 NT$3,055 per night from Jan 20 to Jan 21
NT$3,055
NT$3,586 total
Jan 20 - Jan 21
includes taxes & fees
8/10 Very Good! (9,772 reviews)
Room was noce

Reviewed on 2026/1/15

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$4,114 per night from Feb 1 to Feb 2
NT$4,114
NT$5,756 total
Feb 1 - Feb 2
includes taxes & fees
8.4/10 Very Good! (2,543 reviews)
Great. Did not put us in king size bed as ordered. Did not have washcloths/makeup cloths. They fixed all upon asking. Great service overall. Would stay again.

Reviewed on 2026/1/18

Hilton Chicago
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 NT$2,536 per night from Jan 25 to Jan 26
NT$2,536
NT$2,977 total
Jan 25 - Jan 26
includes taxes & fees
8.8/10 Excellent! (3,730 reviews)
Yes

Reviewed on 2026/1/17

Hilton Chicago/Magnificent Mile Suites
See all 5,103 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 NT$14,924. 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

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

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

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

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy 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 featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

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

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