West Loop Holidays

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    Save up to S$1,300 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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Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was S$908, price is now S$611 per person
S$611
per person
20 Sept - 23 Sept
found 18 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Our room this time was more cozy (re: small). Bathroom was efficient (re: cramped). I would guess they took a suite and made an extra room of it. Staff was great, hotel clean. Just a bad draw in the room - we arrived late.

Reviewed on 27 Jun, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,264, price is now S$850 per person
S$850
per person
20 Sept - 23 Sept
found 18 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (1,813 reviews)
Best location on Michigan Avenue

Reviewed on 27 Jun, 2026

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Price was S$973, price is now S$684 per person
S$684
per person
20 Sept - 23 Sept
found 18 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.4/10 Very good! (3,950 reviews)
The Whitehall is “my Go To” when I am traveling solo, or with a girlfriend! Location is best in the city, for high end shopping and restaurants! Lake Michigan and Oak Street Beach are a “stones throw” away. This is one of the Real Classic Hotels. It is a bit dated, yet; all of my needs are met, with awesome beds, crisp clean linens, luggage racks, a safe for your valuables, along with marble bathrooms, really Hot Showers! The staff is always polite and helpful. The rooms are spacious and views can be awesome!😎 As a 25 year Chicagoan, whom no longer lives here, I Love 💕 this place… 👏 👏 👏

Reviewed on 26 Jun, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,152, price is now S$820 per person
S$820
per person
20 Sept - 23 Sept
found 18 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
Views were amazing on the water with a bonus fireworks show. Thanks Sable!

Reviewed on 26 Jun, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,862, price is now S$1,331 per person
S$1,331
per person
20 Sept - 23 Sept
found 6 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
Great location, wonderful staff.

Reviewed on 26 Jun, 2026

Where to stay in West Loop

Find the best West Loop areas and neighborhoods for the activities you enjoy most. Learn more about West Loop
A busy city street with tall buildings, a bus, and cars.

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 West Loop

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$233 per night from 1 Jul to 2 Jul
S$233
1 Jul - 2 Jul
includes taxes & fees
9/10 Wonderful! (2,302 reviews)
"Excellent"

Reviewed on 28 Jun, 2026

Crowne Plaza Chicago West Loop by IHG
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$245 per night from 5 Jul to 6 Jul
S$245
5 Jul - 6 Jul
includes taxes & fees
8.8/10 Excellent! (1,039 reviews)
"Front desk staff here is especially friendly and helpful. This is also so close to the main train station and also the clinton blue line subway which makes it a great spot!"

Reviewed on 28 Jun, 2026

Holiday Inn & Suites Chicago - Downtown by IHG
The Emily Hotel

The Emily Hotel

4 out of 5
311 North Morgan Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$320 per night from 26 Jul to 27 Jul
S$320
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (1,321 reviews)
"Great location, great space in the rooms!!"

Reviewed on 21 Jun, 2026

The Emily Hotel
See all 4,583 properties in West Loop
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 West Loop holiday package cost?
Our West Loop packages, which start from just S$611, are the best way to save money. Handpick your favourite flights, hotels and rental cars to create a personalized getaway.
How do I get a cheap travel package to West Loop?
If you love bargains, bundle your bookings into a West Loop holiday package. Whether you need flights, hotels, tours or rental cars, you can browse and book them all in one place. You'll have lots of choice at your fingertips as well. Expedia has more than 550 air carriers and 1,000,000 hotels worldwide to select from. Fly with who you want, book a room where you like and save some cash — now that's the ideal getaway!
Where should I stay in West Loop?
Make sightseeing easier by staying someplace just around the corner from West Loop's biggest attractions. University of Illinois Chicago and United Centre are two which top many visitors' bucket lists.
What are the top hotels in West Loop?
Book a room at The Hoxton Chicago. It's one of this area's most sought-after hotels. Another great option in West Loop is Hyatt House Chicago West Loop.
How far in advance should I book my West Loop holiday?
It can be hard to know when the best time is to book your holiday to West Loop. But generally the earlier you book, the more affordable the prices. In some cases, you can lock in your flights and hotels up to a year prior to your departure date. If you're considering a last-minute getaway, no need to stress! There are fantastic deals advertised on Expedia every single day.
What does an Expedia West Loop travel package include?
Hotels, flights and a reliable car for your road trip adventures. Simply select your preferred bundle and get access to great discounts. Once you've made your booking, add on a few sightseeing tours and watch your savings pile up. When it comes to planning your West Loop getaway, you're in charge!
What should I know before booking a West Loop travel package?
Whether it's relaxation or adventure you're chasing, a West Loop holiday package lets you plan your escape your way. Plus, you'll get access to great discounts just for combining your hotel with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with a West Loop Expedia holiday package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines worldwide. Our holiday packages give you the flexibility to take your pick of available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my West Loop holiday package?
Don't stress if you're rethinking your West Loop holiday package — you can cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We know life can occasionally throw a spanner in the travel works, so make your way to our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.

Stay near popular West Loop attractions

Mary Bartelme Park

After visiting Mary Bartelme Park, make a plan to see the other sights and activities in Chicago. Experience the acclaimed art galleries and fascinating museums in this vibrant area.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

S$31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

S$52
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

S$31
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.