West Side Holidays from AU$807

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The Latest West Side Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
30 Sept - 3 Oct
found 22 hours ago
Return flight included
Dallas (DFW) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
Hard to sleep at night due to noise.

Reviewed on 20 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
30 Sept - 3 Oct
found 22 hours ago
Return flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Just a great property- really a 5 star experience-great location

Reviewed on 20 Jul. 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
30 Sept - 3 Oct
found 22 hours ago
Return flight included
Dallas (DFW) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
An amazing property and staff. Will be coming back!

Reviewed on 20 Jul. 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
30 Sept - 3 Oct
found 22 hours ago
Return flight included
Dallas (DFW) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
The property in itself was not terrible, but I expected better.

Reviewed on 19 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
Save 100% on your flight
per person
30 Sept - 3 Oct
found 22 hours ago
Return flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
Beautiful property, will definitely stay there again.

Reviewed on 19 Jul. 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$296 per night from 10 Aug to 11 Aug
AU$296
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (1,279 reviews)
"Great stay - two weeks of wonderful service and attentive front desk. It made my trip worth it!"

Reviewed on 18 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$323 per night from 21 Aug to 22 Aug
AU$323
21 Aug - 22 Aug
includes taxes & fees
8.2/10 Very Good! (1,010 reviews)
"Its was very nice and pleasant stay"

Reviewed on 15 Jul. 2025

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 AU$554 per night from 21 Aug to 22 Aug
AU$554
21 Aug - 22 Aug
includes taxes & fees
9/10 Wonderful! (1,133 reviews)
"Great place"

Reviewed on 19 Jul. 2025

The Emily Hotel
See all 772 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

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
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 entertainment choices 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$75
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$69
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
94% 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$807. 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.