West Side Vacation Packages
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Top West Side Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,193
per person
Nov 20 - Nov 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
Pablo was amazing and he made my 50th birthday experience amazing . Thank you for the champagne and cake surprise . Super recommended .
Reviewed on Sep 1, 2026
Four Seasons Hotel Chicago
Downtown Chicago
CA $2,173
per person
Nov 6 - Nov 9
found 15 hours ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The staff was so kind and helpful. Great location and dining options. The room was spotless and comfortable
Reviewed on Aug 30, 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 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.
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.
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.
Fulton Market
If you're spending some time in Fulton Market, Packer Schopf Gallery and Bar La Rue are top sights worth seeing.
Ready to book your vacation to West Side?
West Side Hotel Deals
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street Chicago IL
Fully refundable
CA $267
CA $318 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (2,585 reviews)
"Great location for downtown. Staff were helpful. Elevator area smelled like cigarette smoke. Bathroom in my room had facial shavings on the counter top, my view was a dirty dumpster area. The fridge in the room came out of a dorm room with no free water for the cost of $450 for the night. Breakfast ..."
Reviewed on Sep 1, 2026
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street Chicago IL
Fully refundable
CA $230
CA $290 total
Sep 7 - Sep 8
includes taxes & fees
Hotel Chicago West Loop, SureStay Collection by Best Western
1622 W Jackson Blvd Chicago IL
Fully refundableReserve now, pay when you stay
CA $192
CA $228 total
Sep 2 - Sep 3
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 collegiate vibe at University of Illinois Chicago during your stay in Chicago. Stroll along the riverfront or experience the acclaimed art scene 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 theater 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 theater 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 scene in this vibrant area.
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.
What to do in West Side
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $56
per adult
94% of travellers recommend
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 $1,185. 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.
Explore a world of travel with Expedia
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- The Loop Vacations
- Chicago Theatre
- Wrigley Field
- Visit The Loop
- Willis Tower
- Art Institute of Chicago
- Millennium Park
- Chicago Vacations
- Lincoln Park Zoo
- Garfield Park Conservatory
- Grant Park
- Ernest Hemingway Museum and House
- Unity Temple
- 875 North Michigan Avenue
- Visit West Loop
- United Center
- Robie House
- Montrose Beach
- Lakeview Vacations
- Water Tower Place
- Rosemont Vacations
- Chicago Riverwalk
- Downtown Chicago Vacations
- Visit Magnificent Mile
- Marina City
- Griffin Museum of Science and Industry
- Visit Downtown Chicago
- Frank Lloyd Wright Historic District
- Buckingham Fountain
- Ann and Robert H. Lurie Children's Hospital
- Navy Pier
- Northwestern University
- Visit Chicago
- International Museum of Surgical Science
- Golf Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
