West Side Holidays
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Top Flight + Hotel Deals in West Side
Price found within the past 48 hours. Click for updated prices.
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
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.
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.
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.
Humboldt Park
While Humboldt Park isn't home to many top sights, Garfield Park Conservatory and National Museum of Puerto Rican Arts & Culture are some notable places to visit nearby.
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.
Top hotels in West Side
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street Chicago IL
Fully refundable
€168
11 Nov - 12 Nov
includes taxes & fees
8.6/10 Excellent! (1,248 reviews)
"Beds were nice to come back to after a long day."
Reviewed on 14 Oct 2026
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
€170
15 Nov - 16 Nov
includes taxes & fees
The Emily Hotel
311 North Morgan Street Chicago IL
€269
15 Nov - 16 Nov
includes taxes & fees
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
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 theatre scene.
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 fascinating museums in this vibrant area.
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 galleries in this vibrant area.
Garfield Park Conservatory
9.0/10 (6 reviews)
While away the afternoon in this huge conservatory housing tropical and rare plants, waterfalls and art.
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 theatre scene in this vibrant area.
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.
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 theatre scene and fascinating museums in this vibrant area.
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.
What to do in West Side
A Remarkable Scavenger Hunt: The Great Quest in Illinois
€11
per adult
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 €762. 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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- Advocate Illinois Masonic Medical Center
- Ann and Robert H. Lurie Children's Hospital
- Apollo Theater Chicago
- Berwyn Holidays
- Buckingham Fountain
- Canalport Riverwalk Park
- Chicago Board of Trade Building
- Visit Chinatown
- Visit Lower West Side
- Visit Near West Side
- Visit Noble Square
- Visit North Lawndale
- Chicago Place Mall
- Chicago Riverwalk
- Visit Smith Park
- Visit United Center
- Chicago Holidays
- Credit Union 1 Arena
- Crown Fountain
- Daley Plaza
- Ernest Hemingway Museum and House
- Frank Lloyd Wright Historic District
- Garfield Park Conservatory
- Grant Park
- Lincoln Hall
- Lincoln Park Zoo
- Millennium Park
- Newberry Library
- Oak Park Holidays
- Prentice Women's Hospital
- River Forest Holidays
- Second Franklin Building
- University of Illinois Chicago
- Water Tower Place
- Willis Tower
- Wrigley Building
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
