West Side Vacation Packages

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Top West Side Vacation Deals

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

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 4 - Jul. 7
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Gorgeous views, great in room dining, staff were very nice

Reviewed on Apr. 28, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 5 - Jun. 9
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,605 reviews)
TV did not work. Was told that it was a problem with the system for everyone and would be fixed in 10 minutes. An hour later I called again and was told the engineer would come to our room next. The engineer never came. No follow up from anyone else. The TV did not work until the next day.

Reviewed on Apr. 29, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 5 - Jun. 9
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,665 reviews)
Good room, comfortable bed, excellent location.

Reviewed on Apr. 26, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 5 - Jun. 9
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9/10 Wonderful! (1,046 reviews)
I stay here everytime I visit home. Great space and location.

Reviewed on Apr. 29, 2025

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 5 - Jun. 9
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Great property in Chicago. Quiet rooms

Reviewed on Apr. 28, 2025

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
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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

Ready to book your vacation to West Side?

 

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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 CA $169 per night from May 27 to May 28
CA $169
CA $198 total
includes taxes & fees
May 27 - May 28
8.8/10 Excellent! (1,002 reviews)
"Great stay."

Reviewed on Apr. 28, 2025

Crowne Plaza Chicago West Loop by IHG
The Emily Hotel
The Emily Hotel
4 out of 5
311 North Morgan Street, Chicago, IL
The price is CA $242 per night from May 22 to May 23
CA $242
CA $284 total
includes taxes & fees
May 22 - May 23
9/10 Wonderful! (1,077 reviews)
"Excellent service"

Reviewed on Apr. 27, 2025

The Emily Hotel
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 CA $185 per night from May 26 to May 27
CA $185
CA $218 total
includes taxes & fees
May 26 - May 27
8/10 Very Good! (1,011 reviews)
"The floors were dirty as if they don't even mop....not really close to anything....construction is going on"

Reviewed on Apr. 29, 2025

Holiday Inn & Suites Chicago - Downtown by IHG
See all 759 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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a West Side vacation package cost?
Be ready to book, because a trip to West Side starts from an affordable CA $842. 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 vacation 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 vacation 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 vacation fantasies.
What are the top hotels in West Side?
Grace Abbott Homes is one place that most travelers 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 vacation?
It can be tricky to know exactly when the best time is to book your West Side vacation. 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 traveling 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 vacation 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 vacation package?
Don’t worry if you’re rethinking your West Side vacation 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.

Discover the most popular places to visit in West Side

United Center

United Center

4.5/5(96 reviews)

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

United Center
Garfield Park Conservatory featuring a park

Garfield Park Conservatory

While away the afternoon in this huge conservatory housing tropical and rare plants, waterfalls and art.

Garfield Park Conservatory
Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field

What to do in West Side

Urbana–Champaign Scavenger Hunt: Hunting Illini

Self-Guided Illinois Scavenger Hunt: The Great Quest in Illinois

CA $17
per adult
Self-Guided Illinois Scavenger Hunt: The Great Quest in Illinois
Flyover in Chicago

Flyover in Chicago

CA $53
per adult
98% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

CA $67
per adult
94% of travellers recommend
Architecture River Tour
See all activities in West Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.