River West 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.
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
Price was S$6,248, price is now S$6,036 per person
S$6,036
per person
3 Feb - 8 Feb
found 3 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,159 reviews)
Clean room, beautiful view and friendly staff

Reviewed on 15 Dec, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was S$7,531, price is now S$6,782 per person
S$6,782
per person
3 Feb - 8 Feb
found 3 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.

Reviewed on 14 Dec, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was S$6,441, price is now S$6,183 per person
S$6,183
per person
3 Feb - 8 Feb
found 3 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Concierge not helpful and neither is was the door man, Neither would get me a cab, they said to just stand outside

Reviewed on 4 Dec, 2025

Nobu Hotel Chicago

Nobu Hotel Chicago

5 out of 5
Downtown Chicago
Price was S$7,326, price is now S$7,046 per person
S$7,046
per person
3 Feb - 8 Feb
found 3 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (748 reviews)
It was fine. I expected more for $1000/ night

Reviewed on 16 Dec, 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was S$6,257, price is now S$6,047 per person
S$6,047
per person
3 Feb - 8 Feb
found 3 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
The staff was outstanding. A great place to stay.

Reviewed on 17 Dec, 2025

Where to stay in River West

Find the best River West areas and neighborhoods for the activities you enjoy most. Learn more about River West
Downtown Chicago which includes 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

Top hotels in River West

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 S$123 per night from 5 Jan to 6 Jan
S$123
5 Jan - 6 Jan, 2026
includes taxes & fees
8.8/10 Excellent! (3,482 reviews)
Room was clean

Reviewed on 14 Dec, 2025

Hilton Chicago/Magnificent Mile Suites
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (2,111 reviews)
Walked to Millers Pub for Tom and Jerry’s, went to the Kringle market and rode the train to Wrigley felt very safe in the area. Room was clean and beautiful and you could feel the history of the hotel as soon as you walked in will definitely be staying again!!!!

Reviewed on 10 Dec, 2025

Get rates
Silversmith Hotel Chicago Downtown
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
75 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$118 per night from 16 Jan to 17 Jan
S$118
16 Jan - 17 Jan, 2026
includes taxes & fees
8.6/10 Excellent! (1,989 reviews)
Very clean and the staff was wonderful!

Reviewed on 13 Dec, 2025

Club Quarters Hotel Wacker at Michigan, Chicago
See all 4,760 properties in River West
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 River West holiday package cost?
Starting from an incredible S$6,036, you can create your own River West holiday package. Simply combine flights, hotels and car rentals and be rewarded with discounts.
How do I get a cheap travel package to River West?
If you love bargains, bundle your bookings into a River West holiday package. Whether you need flights, hotels, activities or rental cars, you can browse and book everything in one place. You'll have a wealth of choice at your fingertips too. Expedia has more than 550 air carriers and 1,000,000 hotels all over the world to pick from. Fly with who you want, stay where you like and save your hard-earned money — now that's the ideal getaway!
Where should I stay in River West?
Most visitors to River West include University of Illinois Chicago and United Centre on their itineraries. Why not consider a hotel that's close to these iconic attractions?
What are the top hotels in River West?
Whether you'll be staying for one or several nights in River West, you'll get a solid night's sleep at Ginosi 747 Apartel. This option is a favourite with lots of travellers.
How far in advance should I book my River West holiday?
It can be difficult to know when is the ideal time to book your holiday to River West. But usually the earlier you book, the cheaper the prices. Sometimes, you can reserve your flights and hotels up to 12 months before departure. If you're considering a last-minute getaway, no need to panic! There are fabulous deals posted on Expedia every day.
What does an Expedia River West travel package include?
Expedia has all you need to plan your River West trip, but how you structure your package depends on you. Pick from any combination of rental cars, hotels and flights. Searching for some activities to fill in your time? Once you've made your booking, you can add them too. Whatever your budget, there's a deal to suit your needs.
What should I know before booking a River West travel package?
Discover deals that suit your budget with an Expedia package. Hotels, flights, rental cars — we've got all of them. You'll save loads just for combining your bookings. Whether you're taking off on a winter adventure or sipping cocktails on a beach, your dream getaway is just a few clicks away.
Can I choose my airline with a River West Expedia holiday package?
Expedia offers access to more than 550 airline partners worldwide, so you definitely can. Just select your preferred carrier and craft your ideal River West trip.
If I'm not able to travel, can I cancel my River West holiday package?
It's good to know that you can cancel your River West booking if your travel plans have changed. Whether you'll be charged a fee or not depends on your hotel, airline or car rental company. It may be possible to change or cancel for free if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.

Popular places to visit

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

Wrigley Field

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

McCormick Place

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
Soldier Field showing a city, modern architecture and a skyscraper

Soldier Field

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field

Things to do

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$52
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Art Institute of Chicago

Art Institute of Chicago

S$52
per adult
92% of travellers recommend
Art Institute of Chicago
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

S$263
per adult
80% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner 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. 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.