West Side Holidays

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Top Flight + Hotel Deals in West Side

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was €5,523, price is now €4,697 per person
€4,697
per person
1 Oct - 7 Oct
found 16 hours ago
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €6,131, price is now €5,273 per person
€5,273
per person
1 Oct - 7 Oct
found 16 hours ago
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €5,626, price is now €4,842 per person
€4,842
per person
1 Oct - 7 Oct
found 16 hours ago
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (1,136 reviews)
Excellent location. Staff very nice. Room big and bed very comfortable. But noisy. As is all of Chicago. Trying to sell in room soap products for exorbitant prices tachy as hell. Rooftop lounge had sadly very short hours and limited open days. Seems a shame to waste such an opportunity.

Reviewed on 14 Jul 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €5,500, price is now €4,878 per person
€4,878
per person
1 Oct - 7 Oct
found 16 hours ago
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
The check in was seamless. Lobby spotless. Room was very clean and tidy. Rooftop area was super.

Reviewed on 12 Jul 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was €5,458, price is now €4,885 per person
€4,885
per person
1 Oct - 7 Oct
found 16 hours ago
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (1,388 reviews)
Beautiful hotel with nice city views. Friendly staff. So many hidden fees, doubled the cost.

Reviewed on 12 Jul 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 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 €203 per night from 10 Aug to 11 Aug
€203
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (2,382 reviews)
"The room was super outdated. The TV was like from the 90s. The AC unit was non-responsive and was blowing cold air the whole night despite it being winter and being set to "heat". Even had to unplug the unit manually. The alarm clock was set to 5am for some reason and had no visible way of being ..."

Reviewed on 15 Jul 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 €158 per night from 16 Aug to 17 Aug
€158
16 Aug - 17 Aug
includes taxes & fees
8.6/10 Excellent! (1,072 reviews)
"Nothing"

Reviewed on 15 Jul 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 €260 per night from 26 Jul to 27 Jul
€260
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (1,312 reviews)
"The check in was seamless. Lobby spotless. Room was very clean and tidy. Rooftop area was super."

Reviewed on 12 Jul 2026

The Emily Hotel
See all 803 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.

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

A Remarkable Scavenger Hunt: The Great Quest in Illinois

A Remarkable Scavenger Hunt: The Great Quest in Illinois

€11
per adult
A Remarkable Scavenger Hunt: The Great Quest in Illinois
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€21
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€40
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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 €4,697. 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.

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.