West Side Holidays

Book a Hotel + Flight or Car together to unlock savings

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
Default Image

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 3.824.908 ₫ per night from 24 Aug to 25 Aug
3.824.908 ₫
4.490.059 ₫ total
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (1,324 reviews)
"It is renovated, it is very clean, the breakfast was delicious"

Reviewed on 30 Jul 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 4.113.086 ₫ per night from 1 Sept to 2 Sept
4.113.086 ₫
5.142.728 ₫ total
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
Convenient location
"Very close to Clinton blue line if you plan on taking public transportation. Quiet hotel with roof top pool. The staff were friendly and helpful. Our only complaint was how tight the bathroom was. For a family you couldn’t fit more than one in the bathroom to get ready at once."

Reviewed on 29 Jul 2025

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
9/10 Wonderful! (1,149 reviews)
"Everything was excellent"

Reviewed on 29 Jul 2025

Get rates
The Emily Hotel
See all 776 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

4.5/5(15 reviews)

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
Humboldt Park

Humboldt Park

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 art galleries and entertainment choices in this vibrant area.

Humboldt Park
Garfield Park Conservatory which includes a park

Garfield Park

After visiting Garfield Park, make a plan to see the other sights and activities in Chicago. Discover the top-notch restaurants and acclaimed art galleries in this vibrant area.

Garfield Park

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 . 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 1null000null000 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.