West Side Vacation Packages

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Top West Side Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was CA $1,019, price is now CA $639 per person
CA $639
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Close to walk most places. Lots of restaurants in the surrounding area. Staff very nice. Rooms clean and spacious.

Reviewed on Aug. 22, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,859, price is now CA $1,126 per person
CA $1,126
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on Aug. 19, 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,505, price is now CA $912 per person
CA $912
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.

Reviewed on Aug. 21, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $2,052, price is now CA $1,250 per person
CA $1,250
per person
Oct 22 - Oct 25
found 17 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug. 10, 2025

Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Downtown Evanston
Price was CA $1,046, price is now CA $662 per person
CA $662
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
7.6/10 Good! (1,000 reviews)
Hotel is beautiful and all of the staff is amazing. Only annoying thing is no free parking. Other than that amazing stay and happy we chose this hotel!

Reviewed on Aug. 18, 2025

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.

Find hotels in West Loop

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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 refundable
The price is CA $249 per night from Aug 24 to Aug 25
CA $249
CA $292 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,396 reviews)
"Great experience. Close to everything."

Reviewed on Aug. 20, 2025

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 refundable
The price is CA $210 per night from Sep 2 to Sep 3
CA $210
CA $263 total
Sep 2 - Sep 3
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"It's not right downtown but close enough... a good little walk to here and there... not bad. I'd stay again if opportunity arises"

Reviewed on Aug. 19, 2025

Holiday Inn & Suites Chicago - Downtown by IHG
Hyatt Place Chicago Medical/University District

Hyatt Place Chicago Medical/University District

3 out of 5
1835 W Harrison Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $189 per night from Sep 1 to Sep 2
CA $189
CA $222 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,263 reviews)
"United center"

Reviewed on Aug. 17, 2025

Hyatt Place Chicago Medical/University District
See all 779 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

Discover the most popular places to visit in West Side

United Center

United Center

Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

United Center
Garfield Park Conservatory featuring a park

Garfield Park Conservatory

While away the afternoon in this huge conservatory housing tropical and rare plants, waterfalls and art.

Garfield Park Conservatory
Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field

What to do in West Side

Urbana–Champaign Scavenger Hunt: Hunting Illini

Self-Guided Illinois Scavenger Hunt: The Great Quest in Illinois

CA $17
per adult
Self-Guided Illinois Scavenger Hunt: The Great Quest in Illinois
River tour boat in Chicago

Architecture River Tour

CA $57
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
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 $639. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.