West Side Trips (flight + hotel)

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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

Top hotels in West Side

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 P8,107 per night from Aug 24 to Aug 25
P8,107
P9,517 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,356 reviews)
"Nice hotel and with easy access"

Reviewed on Aug 6, 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 P8,450 per night from Sep 3 to Sep 4
P8,450
P10,605 total
Sep 3 - Sep 4
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"Location is excellent. 2-3 blocks from Union Station (Amtrak & Metra), and a CTA Blue Line stop. About 5 minute walk to the Loop. Some great restaurants within a couple blocks. The hotel is older and a little shop worn, but it was clean and the staff we met were all friendly and helpful. Because ..."

Reviewed on Aug 6, 2025

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

The Emily Hotel

4 out of 5
311 North Morgan Street, Chicago, IL
9/10 Wonderful! (1,159 reviews)
"The Emily was a super nice hotel with very friendly staff and conveniently located near lots of restaurants and bars"

Reviewed on Aug 5, 2025

Get rates
The Emily Hotel
See all 769 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.

Popular places to visit

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 which includes a garden

Garfield Park Conservatory

This striking conservatory – home to rare tropical plants and decorated with art and water features – provides a beautiful hiatus from the hectic pace of Chicago.

Garfield Park Conservatory
McCormick Place

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place

What to do in West Side

Urbana–Champaign Scavenger Hunt: Hunting Illini

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

P716
per adult
Self-Guided Illinois Scavenger Hunt: The Great Quest in Illinois
River tour boat in Chicago

Architecture River Tour

P2,411
per adult
96% of travellers recommend
Architecture River Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

P2,617
per adult
98% of travellers recommend
Chicago Sightseeing River and 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 . 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.