West Side Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in West Side
Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
€1,058
per person
3 Oct - 7 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very good! (3,932 reviews)
Hotel look is a bit dated but location is great! Friendly and helpful staff with great views of city
Reviewed on 31 Aug 2026
Hotel Riu Plaza Chicago
Downtown Chicago
€1,431
per person
3 Oct - 7 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Loved it and definitely feel like the bathroom was made for the girls! Just wish we had gotten a response for requests we madr but other than that it was a good hotel! Loved the breakfast.
Reviewed on 31 Aug 2026
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.
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.
Fulton Market
If you're spending some time in Fulton Market, Packer Schopf Gallery and Bar La Rue are top sights worth seeing.
Top hotels in West Side
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street Chicago IL
Fully refundable
€198
7 Sept - 8 Sept
includes taxes & fees
9/10 Wonderful! (2,579 reviews)
"Really clean!had a great experience"
Reviewed on 31 Aug 2026
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street Chicago IL
Fully refundable
€163
7 Sept - 8 Sept
includes taxes & fees
8.6/10 Excellent! (1,196 reviews)
"Rooftop pool is so cool! The neighbors on our floor were quite noisy."
Reviewed on 30 Aug 2026
Hotel Chicago West Loop, SureStay Collection by Best Western
1622 W Jackson Blvd Chicago IL
Fully refundableReserve now, pay when you stay
€159
1 Sept - 2 Sept
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 fascinating museums.
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.
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.
Garfield Park Conservatory
9.0/10 (6 reviews)
While away the afternoon in this huge conservatory housing tropical and rare plants, waterfalls and art.
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.
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.
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.
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.
What to do in West Side
A Remarkable Scavenger Hunt: The Great Quest in Illinois
€11
per adult
Chicago: Navy Pier Centennial Wheel Ticket
€21
per adult
90% of travellers recommend
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 €1,058. 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.
Explore a world of travel with Expedia
- 3 Star Hotels in Chicago
- 4 Star Hotels in Chicago
- Hotels near Anna and Frederick Douglass Park
- Hotels near Cadillac Palace Theatre
- Aparthotels in Chicago
- Hostels in Chicago
- Affinia Hotels in Chicago
- Boutique Hotels in Chicago
- Historic Hotels in Chicago
- Hotels with Bar in Chicago
- Hotels with Breakfast in Chicago
- Hotels with Pool in Chicago
- La Quinta Inn & Suites Hotels in Chicago
- Lgbt-Friendly Hotels in Chicago
- Motel 6 Hotels in Chicago
- Pet Friendly Hotels in Chicago
- Wyndham Hotels in Chicago
- Chicago Hotels
- Chinatown Hotels
- Beach Hotels in Cicero
- Hotels near Credit Union 1 Arena
- Hotels with Spa in Downtown Chicago
- Downtown Chicago Hotels
- East Garfield Park Hotels
- East Village Hotels
- Oakwood Hotels in Grace Abbott Homes
- Hotels near Holy Innocents Church
- Humboldt Park Hotels
- Little Italy Hotels
- Little Village Hotels
- Lower West Side Hotels
- Hotels near Michigan Avenue
- Near South Side Hotels
- Near West Side Hotels
- North Lawndale Hotels
- Cheap Hotels in Oak Park
- River North Hotels
- Lgbt-Friendly Hotels in South Loop
- Hotels near St. John Cantius Church
- Boutique Hotels in The Loop
- Hotels with Bar in The Loop
- Hotels with Yoga in The Loop
- The Loop Hotels
- Tri-Taylor Hotels
- Ukrainian Village Hotels
- United Center Hotels
- Hotels near United Center
- Cheap Hotels in West Loop
- Marriott Hotels & Resorts in West Loop
- Hotels with Spa in West Loop
- West Loop Hotels
- Aparthotels in West Side
- Hostels in West Side
- West Town Hotels
- Wicker Park Hotels
- Hotels near Willis Tower
- 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.
