West Loop Holidays from AU$2,541

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$2,500 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

Your West Loop Holiday

Avoid the hassle of travel planning with a West Loop holiday package. With everything organised before you go, all that's left to do is enjoy this riverside neighbourhood's cafes, bars and pubs and dining. Some leading nearby attractions to check out during your trip to West Loop include University of Illinois Chicago, United Centre and Anna and Frederick Douglass Park. Expedia will help turn your dream West Loop holiday into reality, whatever your travel plans or budget.

Top Holiday Package Deals in West Loop

Price found within the past 48 hours. Click for updated prices.
Hotel Weston RFD

Hotel Weston RFD

2.5 out of 5
Price was AU$2,571, price is now AU$2,541 per person
AU$2,541
per person
21 Sept - 23 Sept
found 18 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
5.4/10 (180 reviews)
Property did not have a secure lock, the room was not clean and people were fixing cars on the property.

Reviewed on 13 July 2026

White Pines Lodge

White Pines Lodge

2 out of 5
Price was AU$2,714, price is now AU$2,647 per person
AU$2,647
per person
21 Sept - 23 Sept
found 18 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (53 reviews)
Definitely rustic. Cozy cabin that was outdated, but generally clean. If you’re looking for an outdoor experience, this is a good place. Two issues stand out for us: 1) the “queen” bed was horrible. It seemed it was for Lilliputians. My wife and I are practically beat each other all night. All things considered, sleeping should be comfortable. For this reason alone we would not sleep here again. 2) the air conditioning vent blew right on us. It was either hot or freezing. Nice park to visit, but wouldn’t stay here.

Reviewed on 9 July 2026

Riverview Inn & Suites, an Ascend Collection Hotel

Riverview Inn & Suites, an Ascend Collection Hotel

3 out of 5
Price was AU$2,644, price is now AU$2,603 per person
AU$2,603
per person
21 Sept - 23 Sept
found 18 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
8.4/10 Very good! (1,005 reviews)
Bathroom in Shower was slippery no Matt or Gran bars, food was warm, there was only Sausage, can not eat sausage, eggs was real eggs, only had donuts on weekend.

Reviewed on 13 July 2026

Motel 6 Rockford, IL

Motel 6 Rockford, IL

2 out of 5
Price was AU$2,573, price is now AU$2,543 per person
AU$2,543
per person
21 Sept - 23 Sept
found 18 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
6.6/10 (467 reviews)
This was just a stop over less than 12 hours. The room only appeared clean to the eye. Hair in shower so I didn’t use it and when I left in morning saw a few bugs. Heavy musty moldy smell and the ac smelled like cigarette smoke.

Reviewed on 8 July 2026

Clayton House Motel

Clayton House Motel

2.5 out of 5
Price was AU$2,586, price is now AU$2,560 per person
AU$2,560
per person
21 Sept - 23 Sept
found 18 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
5.8/10 (29 reviews)
The facility could be functional if it was maintained better 1) the air conditioner didn’t work 2) the tub drain was plugged we stood in water over our ankles while showering 3) the floor was dirty 4 ) the light bulb burnt out first night we was there 5 ) no comfort in the beds well worn out mattress

Reviewed on 3 July 2026

Our guide on 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

Our pick of the best West Loop Hotel Deals

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 refundable
The price is AU$323 per night from 13 Aug to 14 Aug
AU$323
13 Aug - 14 Aug
includes taxes & fees
9/10 Wonderful! (2,375 reviews)
"Everything was clean and the food at the Deli was good."

Reviewed on 13 July 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 AU$321 per night from 19 July to 20 July
AU$321
19 July - 20 July
includes taxes & fees
8.6/10 Excellent! (1,075 reviews)
"Clean rooms loved my trip"

Reviewed on 13 July 2026

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

The Emily Hotel

4 out of 5
311 North Morgan Street Chicago IL
The price is AU$428 per night from 26 July to 27 July
AU$428
26 July - 27 July
includes taxes & fees
9.2/10 Wonderful! (1,335 reviews)
"The check in was seamless. Lobby spotless. Room was very clean and tidy. Rooftop area was super."

Reviewed on 12 July 2026

The Emily Hotel
See all 4,510 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a West Loop holiday package cost?
Our West Loop packages, which start from just AU$2,541, 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

Union Park

After visiting Union Park, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.
See properties

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$39
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

AU$58
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$36
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.