West Side Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to €185 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

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

Top Flight + Hotel Deals in West Side

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 €1,443, price is now €873 per person
€873
per person
4 Oct - 10 Oct
just found
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Great location and room was fantastic! Only negatives were a lengthy check in and access to the outside deck was closed at 10 PM. Probably a good idea for that, but it would’ve been nice to go out there for a nightcap.

Reviewed on 26 Aug 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €1,794, price is now €1,081 per person
€1,081
per person
4 Oct - 10 Oct
just found
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Will be coming back! Beautiful rooms and great staff.

Reviewed on 24 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was €2,271, price is now €1,396 per person
€1,396
per person
2 Nov - 7 Nov
found 12 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was €1,722, price is now €1,066 per person
€1,066
per person
4 Oct - 10 Oct
just found
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (666 reviews)
The hotel never got cool, hot everywhere, even the community areas. We had to use the TV in the communal area as ours didn't work. We called on day one and the girl laughed and never sent anyone to fix it. Our key cards didn't work multiple times during the stay. The party that happened at the pool on Sunday night of our stay was awful. I couldn't imagine what my kids saw even those this hotel said no parties.

Reviewed on 25 Aug 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was €1,713, price is now €1,117 per person
€1,117
per person
4 Oct - 10 Oct
just found
Return direct flight included
Dublin (DUB) 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 21 Aug 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
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 €181 per night from 1 Sept to 2 Sept
€181
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,402 reviews)
"It was a 10 out of 10. Definitely will be booking here again."

Reviewed on 22 Aug 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 €162 per night from 2 Sept to 3 Sept
€162
2 Sept - 3 Sept
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
"Maurice"

Reviewed on 22 Aug 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 €136 per night from 1 Sept to 2 Sept
€136
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,271 reviews)
"$30 per night for parking. New hotel, nice bar on second floor."

Reviewed on 25 Aug 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.

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
University of Illinois Chicago

University of Illinois Chicago

Enjoy the student vibe at University of Illinois Chicago during your visit to Chicago. Stroll along the riverfront or experience the acclaimed art galleries in this vibrant area.

University of Illinois Chicago
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

What to do in West Side

Urbana–Champaign Scavenger Hunt: Hunting Illini

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

€11
per adult
Self-Guided Illinois Scavenger Hunt: The Great Quest in Illinois
River tour boat in Chicago

Architecture River Tour

€36
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

€35
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in West Side

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 €873. 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 1,000,000 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.