West Side Holidays from AU$2,912

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The Latest West Side Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Spark by Hilton Merrillville

Spark by Hilton Merrillville

3 out of 5
Price was AU$2,957, price is now AU$2,912 per person
AU$2,912
per person
27 Sept - 4 Oct
found 17 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (52 reviews)
Excellent all around, very nice place to stay.

Reviewed on 24 Aug. 2025

Hilton Garden Inn Merrillville

Hilton Garden Inn Merrillville

3 out of 5
Green Acres
Price was AU$3,547, price is now AU$3,196 per person
AU$3,196
per person
27 Sept - 4 Oct
found 17 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
The staff were absolutely wonderful. Everything was clean and they had an open bar and the bartender was absolutely amazing. The lady at the front desk couldn’t have been more helpful. It had been a long trip and they were right there, waiting on us hand and foot.

Reviewed on 19 Aug. 2025

Hampton Inn by Hilton Merrillville

Hampton Inn by Hilton Merrillville

2.5 out of 5
Price was AU$3,115, price is now AU$2,930 per person
AU$2,930
per person
27 Sept - 4 Oct
found 17 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.6/10 Excellent! (805 reviews)
Convenient to shops and restaurants.

Reviewed on 2 Aug. 2025

Tru By Hilton Merrillville

Tru By Hilton Merrillville

2.5 out of 5
Price was AU$3,074, price is now AU$3,020 per person
AU$3,020
per person
27 Sept - 4 Oct
found 17 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (273 reviews)
Property was clean and the staff was outstanding.

Reviewed on 26 Aug. 2025

Homewood Suites by Hilton Munster

Homewood Suites by Hilton Munster

3 out of 5
Price was AU$3,033, price is now AU$2,981 per person
AU$2,981
per person
27 Sept - 4 Oct
found 17 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
I love how kind the staff was , they were amazing!

Reviewed on 22 Aug. 2025

Our guide on where to stay in West Side

Find the best West Side areas and neighborhoods for the activities you enjoy most. Learn more about West Side
Default Image

West Loop

1 out of top 10 points of interest in this area

Consider a visit to Milwaukee Avenue and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center.

Find hotels in West Loop

West Side Holiday

West Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Top Sights
Anna and Frederick Douglass Park, Humboldt Park and Garfield Park

Our pick of the best West Side 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$324 per night from 1 Sept to 2 Sept
AU$324
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,404 reviews)
"I really enjoyed my stay at this hotel!"

Reviewed on 24 Aug. 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$292 per night from 2 Sept to 3 Sept
AU$292
2 Sept - 3 Sept
includes taxes & fees
8.2/10 Very Good! (1,006 reviews)
"We have a Freshman attending UIC this year…literally 3 blocks from her dorm! But the water pressure in the showers leave A LOT to be desired..We have better water pressure in our RV shower..But that’s my only complaint"

Reviewed on 23 Aug. 2025

Holiday Inn & Suites Chicago - Downtown by IHG
Hyatt Place Chicago Medical/University District

Hyatt Place Chicago Medical/University District

3 out of 5
1835 W Harrison Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$246 per night from 1 Sept to 2 Sept
AU$246
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,270 reviews)
"$30 per night for parking. New hotel, nice bar on second floor."

Reviewed on 25 Aug. 2025

Hyatt Place Chicago Medical/University District
See all 779 properties in West Side
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
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All Inclusive Holidays
Cheap Holidays
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beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in West Side

United Center

United Center

5/5(8 reviews)

Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

United Center
University of Illinois Chicago

University of Illinois Chicago

4.5/5(4 reviews)

Enjoy the student vibe at University of Illinois Chicago during your visit to Chicago. Stroll along the riverfront or experience the acclaimed art galleries in this vibrant area.

University of Illinois Chicago
Garfield Park Conservatory showing a garden

Garfield Park Conservatory

This striking conservatory – home to rare tropical plants and decorated with art and water features – provides a beautiful hiatus from the hectic pace of Chicago.

Garfield Park Conservatory

What to do in West Side

River tour boat in Chicago

Architecture River Tour

AU$63
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

AU$69
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in West Side

Frequently asked questions

How much does a West Side holiday package cost?
Be ready to book, because a trip to West Side starts from an affordable AU$2,912. When you combine your flights, hotels and car rentals into a travel package, you'll score the best prices.
How do I get a cheap travel package to West Side?
It's easy. Just bundle. Flights, rental cars and hotels — combine whatever you need into a West Side holiday package to save a pile of cash. Score even better deals when you include extras such as activities or tours to your booking. But that's not the only good part. You have the flexibility to put together your holiday your own way. We offer more than 550 airlines and 1 000 000 hotels across the world, so that everyone has an opportunity to travel and live out those holiday fantasies.
What are the top hotels in West Side?
Grace Abbott Homes is one place that most travellers to West Side include in their itinerary. For a memorable stay here, take a look at Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton.
How far in advance should I book my West Side holiday?
It can be tricky to know exactly when the best time is to book your West Side holiday. But generally the earlier you book, the cheaper the prices. Sometimes, you can lock in your flights and hotels nearly 12 months before departure. If you're thinking of a last-minute getaway, no need to worry! There are terrific deals popping up on Expedia every single day.
What does an Expedia West Side travel package include?
That depends on what you're after. If you're travelling alone, you might decide to bundle flights and hotels. Taking the whole crew to West Side? A travel package that includes rental cars, flights and hotels might suit you better. Expedia gives you the flexibility and freedom to tailor your travel package.
What should I know before booking a West Side travel package?
So many places to travel to, so many things to experience. With a travel package, you can cross more of them off your list. Bundle your flights, hotels and rental cars and get ready to save.
Can I choose my airline with a West Side Expedia holiday package?
Most definitely. Expedia has more than 550 airline partners to select from all over the world. With so much choice, finding the right carrier to get you to West Side shouldn't be hard.
If I'm not able to travel, can I cancel my West Side holiday package?
Don't worry if you're rethinking your West Side holiday package — you can cancel or change 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 fees from your hotel, airline or car rental company. We understand life can sometimes throw a spanner in the works, so make your way to our Customer Service Portal if that happens. When you're ready to make changes, we'll take care of it.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.