Goose Island Holidays

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    Save up to S$134 when you book a flight and hotel together*

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Price found within the past 48 hours. Click for updated prices.
Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop

3 out of 5
Downtown Chicago
Price was S$2,686, price is now S$2,396 per person
S$2,396
per person
29 May - 31 May
found 1 hour ago
Return flight included
Singapore (SIN) to Chicago (ORD)
8.8/10 Excellent! (1,197 reviews)
Room was clean and everything was good. Front desk could be a little more friendly especially one of the afternoon girls.

Reviewed on 5 Mar, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was S$3,187, price is now S$2,412 per person
S$2,412
per person
29 May - 31 May
found 1 hour ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Great location right off of Michigan Ave. They have a very good breakfast, that included almost everything you could want. It was very popular and packed with people. One negative, it felt like it was a cafeteria and not a relaxing place to sit down, relax and enjoy.

Reviewed on 9 Mar, 2026

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was S$2,970, price is now S$2,593 per person
S$2,593
per person
29 May - 31 May
found 1 hour ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,993 reviews)
Friendly staff, very helpful and approachable. The rooms were clean and I pay attention to these things, the room was immaculate upon checkin. I appreciated the lovely in-room espresso machine too. Good breakfast from the onsite restaurant. There’s also coffee, donuts and bubble tea cafes right across Michigan ave. Close to the art institute, the orange and red lines, and more I am sure. Highly recommend the Arlo for your stay in downtown Chicago.

Reviewed on 9 Mar, 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

4.5 out of 5
Downtown Chicago
Price was S$2,896, price is now S$2,583 per person
S$2,583
per person
29 May - 31 May
found 1 hour ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9.2/10 Wonderful! (1,407 reviews)
Check in was quick and easy, room was clean and spacious

Reviewed on 9 Mar, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was S$2,908, price is now S$2,595 per person
S$2,595
per person
29 May - 31 May
found 1 hour ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9/10 Wonderful! (3,285 reviews)
Great stay. Staff was slightly inattentive at times with requests for things to room.

Reviewed on 9 Mar, 2026

Where to stay in Goose Island

Find the best Goose Island areas and neighborhoods for the activities you enjoy most. Learn more about Goose Island
Downtown Chicago which includes a city

Downtown Chicago

4 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 Goose Island

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 S$249 per night from 21 Mar to 22 Mar
S$249
21 Mar - 22 Mar
includes taxes & fees
8/10 Very Good! (9,938 reviews)
Good: Clean; friendly staff. Bad: hot water stopped working at some point; safe was not working; lightbulb kept flickering; ice machine was broken on the 10th floor

Reviewed on 9 Mar, 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 S$242 per night from 18 Mar to 19 Mar
S$242
18 Mar - 19 Mar
includes taxes & fees
9.4/10 Exceptional! (3,498 reviews)
Great location right off of Michigan Ave. They have a very good breakfast, that included almost everything you could want. It was very popular and packed with people. One negative, it felt like it was a cafeteria and not a relaxing place to sit down, relax and enjoy.

Reviewed on 9 Mar, 2026

Hotel Riu Plaza Chicago
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
The price is S$183 per night from 22 Mar to 23 Mar
S$183
22 Mar - 23 Mar
includes taxes & fees
8.6/10 Excellent! (5,745 reviews)
Love the complimentary drinks !

Reviewed on 10 Mar, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,738 properties in Goose Island
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 Goose Island holiday package cost?
Our Goose Island holiday packages, which begin from just S$2,396, are an ideal way to save precious money. Pick and choose your preferred flights, hotels and rental cars to create your ideal getaway.
How do I get a cheap travel package to Goose Island?
Bundle, bundle, bundle. Flights, hotels and rental cars — combine whatever you need into a Goose Island holiday package to save a ton of cash. Score even more discounts when you include extras such as activities or tours to your booking. But that's not the only impressive part. You have the flexibility to customize your holiday your way. We offer more than 550 airlines and 1,000,000 properties worldwide, so that everyone has an opportunity to travel and live out those holiday dreams.
How far in advance should I book my Goose Island holiday?
To score discount prices, book early. Air carriers usually begin selling tickets, along with some of the lowest fares, around 12 months prior to departure. Hotels, car rental and activities should also be booked early so you can have the pick of the bunch. If you're in need of a last-minute getaway in Goose Island, there are always lots of great deals on Expedia. Book your escape today!
What does an Expedia Goose Island travel package include?
Flights, hotels and a cool set of wheels for your road trip adventures. Simply mix and match your favourite bundle and gain access to great discounts. Once you've made your booking, add on a few activities and tours and watch your savings grow. When it comes to creating your Goose Island holiday, you're the one in control!
What should I know before booking a Goose Island travel package?
When you book your hotels, flights and car rentals together, you'll walk away with fantastic discounts. Whether you're planning an island getaway in a villa or would rather stay in a convenient hotel in the city, Expedia can help make it happen.
Can I choose my airline with a Goose Island Expedia holiday package?
Yes — that's one of the best things about an Expedia holiday package. You get to decide. We have more than 550 airline partners around the world, so you have loads of choice when creating your Goose Island adventure.
If I'm not able to travel, can I cancel my Goose Island holiday package?
Plans can change without warning, so yes. You may be able to change or cancel your Goose Island holiday package for free within 24 hours of booking. For older bookings, you can still make changes, but your car rental company, airline or hotel may impose a fee. Looking for more information? Take a look at our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place showing a high rise building and a city

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

4.5/5(147 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

Things to do

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

S$56
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$51
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

S$208
per adult
80% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
See all activities in Chicago

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.