West Side Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by throwingsofas

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top West Side Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Price was CA $1,157, price is now CA $830 per person
CA $830
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very good! (3,941 reviews)
Only stayed there for a day so can’t say much other then 1. A couple times we went downstairs throughout the day and the front desk and lobby was completely empty 2. Not much activity as far as other customers being there I only saw one couple there 3. We arrived a bit early and instead of the lady charging us the $30 for early entrance she charged me $ 4 as far as amenities our room did not had a microwave or much going on other then a small coffee maker

Reviewed on Jul 3, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,038, price is now CA $1,377 per person
CA $1,377
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back. The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.

Reviewed on Jul 2, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,608, price is now CA $1,112 per person
CA $1,112
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,013 reviews)
This location is ideal for families. The amenities provided are exceptional, scoring a perfect ten out of ten. It offers ample space for a family, including two bathrooms, which was greatly appreciated by my children. The property is well-equipped to ensure a comfortable stay. My only reservation pertains to its distance from Michigan Avenue and the Riverwalk, necessitating a vehicle to access these popular destinations. Otherwise, the experience was flawless.

Reviewed on Jul 2, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,758, price is now CA $1,256 per person
CA $1,256
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,128 reviews)
Great property in the heart of the city

Reviewed on Jul 1, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,415, price is now CA $1,015 per person
CA $1,015
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
Traveling as a family of 4 with 2 teenagers and we could not have picked a better place to stay. We were able to see all the sights, eat all the Chicago food and shop until we dropped. I would absolutely stay here again.

Reviewed on Jul 3, 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
A cityscape with modern skyscrapers and a curved highway.

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.

Find hotels in West Loop

Ready to book your vacation to West Side?

 

Choose your dates

West Side Hotel Deals

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $241 per night from Jul 5 to Jul 6
CA $241
CA $287 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (2,323 reviews)
"Cool hotel to stay at. Clean and comfortable. Couple of good nights rest. Gym was better than most hotel gyms. Room was tight. Balcony was nice tho. Really nice area for dining and shopping. Parking for tall cars across the highway which was convenient. Whole Foods across the street. Definitely ..."

Reviewed on Jul 3, 2026

Crowne Plaza Chicago West Loop by IHG
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $241 per night from Jul 5 to Jul 6
CA $241
CA $304 total
Jul 5 - Jul 6
includes taxes & fees
8.6/10 Excellent! (1,047 reviews)
"Love the pool located roof top"

Reviewed on Jul 2, 2026

Holiday Inn & Suites Chicago - Downtown by IHG
The Emily Hotel

The Emily Hotel

4 out of 5
311 North Morgan Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $387 per night from Jul 26 to Jul 27
CA $387
CA $460 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (1,322 reviews)
"Very close to shopping, eating, and interstate. Great location. We walked to most of what we wanted to do."

Reviewed on Jul 2, 2026

The Emily Hotel
See all 805 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular West Side attractions

A large, modern building with a curved facade and multiple vertical windows.

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 entertainment choices.
See properties

What to do in West Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in West Side

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 $830. 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

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