West Loop Holidays from AU$2,169

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to AU$703 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    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 Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
16 Oct - 23 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
It was a great location , close to downtown core.

Reviewed on 30 Jul. 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
16 Oct - 23 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Wonderful hotel in a great location along the river. The view from Terrace 16 is amazing! Also, the pillows on the bed are really comfortable. I love this hotel and would recommend it to anyone.

Reviewed on 30 Jul. 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
16 Oct - 23 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
Finding a park is hard and the process of getting a room is very tedious but still very beautiful I’ve been twice

Reviewed on 29 Jul. 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
16 Oct - 23 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
Excellent location and beautiful property.

Reviewed on 30 Jul. 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
16 Oct - 23 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
The hotel is ok. There’s one actual restaurant and the food is average. Outside of that you can walk to the pier. The main advantage is being on the pier and the hotel really rides that as their main selling point because they can’t stand on their own too much. I stayed recently and had an extra 197 charged to my card that wasn’t on my receipt and I called to see what that was from. The guy who answered the phone answered with “hi. What do you need”. And when I said I wanted to confirm the charge he said what it was and then hung up on me. I’ve never had a hotel be that unfriendly. I work customer service so I know a lot of people can not be great on the phone. But that was unprompted and flat out rude.

Reviewed on 29 Jul. 2025

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
Downtown Chicago featuring 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

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
The price is AU$270 per night from 24 Aug to 25 Aug
AU$270
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (1,320 reviews)
"Great location. Very walkable to restaurants and bars. Not far from Michigan Ave, very quick Uber ride or about a 25 - 30 minute walk. The hotel is very good with very friendly staff. Its clean, but our room was showing some wear and tear. There was some minor mold in ine corner of the tub, the bed ..."

Reviewed on 28 Jul. 2025

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 refundable
The price is AU$309 per night from 24 Aug to 25 Aug
AU$309
24 Aug - 25 Aug
includes taxes & fees
8.2/10 Very Good! (1,030 reviews)
"Reception was polite and helpful..clean hotel..will recommend"

Reviewed on 28 Jul. 2025

Holiday Inn & Suites Chicago - Downtown by IHG
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
354 North Union Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (250 reviews)
"It’s was better than we could have hoped for. Would definitely book again!"

Reviewed on 27 Jul. 2025

Get rates
Level Chicago Fulton Market
See all 4,659 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$2,169, 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.

Activities

Lights, Camera, Action: Chicago Iconic Movie Scenes with In-App Audio Tour

Lights, Camera, Action: Chicago Iconic Movie Scenes with In-App Audio Tour

AU$11
per traveller
Lights, Camera, Action: Chicago Iconic Movie Scenes with In-App Audio Tour
Marvels & Feats: An Engineer's Tour of Chicago Architecture

Marvels & Feats: An Engineer's Tour of Chicago Architecture

AU$53
per adult
Marvels & Feats: An Engineer's Tour of Chicago Architecture
Bike or ebike Bar Hop - RiNo Arts District & Downtown

Bikes, Brews & Hidden Bars: A Ride Through RiNo & Downtown

AU$145
per adult
Bikes, Brews & Hidden Bars: A Ride Through RiNo & Downtown
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.