West Side Vacations

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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 The Old Post Office 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.

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A train at a station with a cityscape in the background.

West Town

2 out of top 10 points of interest in this area

Noted for its live music and theaters, there's plenty to explore in West Town. Top attractions like The Salt Shed and Milwaukee Avenue are major draws, and you can hop on the metro at Division Station or Damen Station to see more of the city.

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Near West Side

4 out of top 10 points of interest in this area

Live music, theaters, and shopping highlight some notable features of Near West Side. Make a stop by United Center or Credit Union 1 Arena while you're visiting, and jump aboard the metro at Polk Station (Pink Line) or Racine Station to get around town.

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Wicker Park

Consider exploring the abundant dining options in Wicker Park. If sightseeing is on the list, Milwaukee Avenue is a top attraction. Hop on the metro at Damen Station or Division Station to see more of the area.

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Humboldt Park

While Humboldt Park might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Garfield Park Conservatory and National Museum of Puerto Rican Arts & Culture.

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Find the Best West Side Vacation Packages

West Side Hotel Deals

Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

506 West Harrison Street Chicago IL
NT$5,934
NT$7,438 total
Oct 25 - Oct 26
includes taxes & fees
Holiday Inn & Suites Chicago - Downtown by IHG
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

25 South Halsted Street Chicago IL
NT$6,020
NT$7,158 total
Oct 25 - Oct 26
includes taxes & fees
9/10 Wonderful! (2,682 reviews)
"Inexplicable que un hotel que pretende ser de esta categoría no tenga piscina. Carísimo el parking del hotel. Desayuno muy básico. Muy buena ubicación."

Reviewed on 2026/9/29

Crowne Plaza Chicago West Loop by IHG
LIVN - West Loop Chicago

LIVN - West Loop Chicago

555 West Jackson Boulevard Chicago IL
NT$5,944
NT$6,978 total
Oct 1 - Oct 2
includes taxes & fees
9.2/10 Wonderful! (305 reviews)
"Our room was very clean and cozy I appreciated all the little details such as bottled water left for our stay and the fact we were provided cleaning supplies and laundry detergent pods for the in room washer very thoughtful. I will definitely book again in the future"

Reviewed on 2026/9/30

LIVN - West Loop Chicago
See all 810 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.

Stay near popular West Side attractions

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United Center

8.8/10 (4,269 reviews)
Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.
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University of Illinois Chicago

8.4/10 (1,058 reviews)
Enjoy the collegiate vibe at University of Illinois Chicago during your stay in Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.
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A riverside path with a stone edge, lush greenery, and yellow flowers.

Humboldt Park

7.0/10 (2 reviews)
Humboldt Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the fascinating museums and acclaimed art scene in this vibrant area.
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A greenhouse with a glass ceiling, various tropical plants, and a central walkway.
Photo by Nina Huang

Garfield Park

After visiting Garfield Park, make a plan to see the other sights and activities in Chicago. Discover the top-notch restaurants and acclaimed theater scene in this vibrant area.
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Anna and Frederick Douglass Park

7.0/10 (12 reviews)
After visiting Anna and Frederick Douglass Park, make a plan to see the other sights and activities in Chicago. Experience the acclaimed theater scene and fascinating museums in this vibrant area.
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The Salt Shed

You can get tickets for a performance at The Salt Shed during your stay in Chicago. Experience the live music and theater scene in this vibrant area.
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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.
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Credit Union 1 Arena

8.0/10 (5 reviews)
Catch an event at Credit Union 1 Arena during your trip to Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.
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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 . 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.