West Side Holidays

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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 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.

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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 theatres, 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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A city skyline with modern skyscrapers, a parking lot, and a distinctive building with a geometric facade.

Near West Side

4 out of top 10 points of interest in this area

Live music, theatres 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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A train crossing an elevated bridge over a city street with buildings and greenery.

Wicker Park

Spend some time visiting places like Milwaukee Avenue while getting to know Wicker Park, and be sure to check out the abundant dining options. You can hop aboard the metro at Damen Station or Division Station to see more of the area.

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Lower West Side

The bars and museums are just a few things visitors like about Lower West Side. National Museum of Mexican Art and The Geraghty are worthwhile spots to check out, and you can hop on the metro at Damen Station (Pink Line) or 18th Station (Pink Line) to get around the larger area.

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Top hotels in West Side

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

25 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
S$262
30 Aug - 31 Aug
includes taxes & fees
Crowne Plaza Chicago West Loop by IHG
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

506 West Harrison Street Chicago IL
Fully refundable
S$254
7 Sept - 8 Sept
includes taxes & fees
Holiday Inn & Suites Chicago - Downtown by IHG
The Emily Hotel

The Emily Hotel

311 North Morgan Street Chicago IL
Fully refundableReserve now, pay when you stay
S$414
30 Aug - 31 Aug
includes taxes & fees
9.2/10 Wonderful! (1,336 reviews)
"Room was very basic, nothing special. Beds were alright but not super comfy. Trains going all day and night were a little annoying but we managed to get used to it and get a decent sleep. Coffee bar on the first floor by lobby was super convenient and helped get the day started."

Reviewed on 15 Aug, 2026

The Emily Hotel
See all 801 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 fascinating museums.
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A cityscape with a prominent skyscraper, a circular building, and a large rectangular building.

University of Illinois Chicago

8.4/10 (1,058 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.
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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 acclaimed theatre scene and fascinating museums in this vibrant area.
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A greenhouse with diverse tropical plants and a large glass structure.

Garfield Park Conservatory

9.0/10 (6 reviews)
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.
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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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The Salt Shed

You can get tickets for a performance at The Salt Shed on your trip to Chicago. Experience the live music and theatre 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 fascinating museums and acclaimed art galleries 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 acclaimed theatre scene in this vibrant area.
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What to do in West Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

S$35
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

S$32
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$52
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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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 . 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.

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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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.