Hillside Holidays

Photo by Joe Farmer

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Top Flight + Hotel Deals in Hillside

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
28 Oct - 2 Nov
found 8 hours ago
Return direct flight included
Shannon (SNN) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
The property is very convenient, but the rooms are extremely small. Our toilet did not work took forever to flush if you’re on the high floors. Not really no views like they said.

Reviewed on 11 Aug 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
per person
28 Oct - 2 Nov
found 8 hours ago
Return direct flight included
Shannon (SNN) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on 12 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
30 Oct - 2 Nov
found 20 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Location, staff and accommodations were excellent.

Reviewed on 13 Aug 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
28 Oct - 2 Nov
found 8 hours ago
Return direct flight included
Shannon (SNN) to Chicago (ORD)
9/10 Wonderful! (654 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on 27 Jul 2025

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
per person
28 Oct - 2 Nov
found 8 hours ago
Return direct flight included
Shannon (SNN) to Chicago (ORD)
9.4/10 Exceptional! (1,927 reviews)
Great location, very convenient. Short walk to a lot of food options. The room furniture could use an update though. You’ll sink right into the bed and couch.

Reviewed on 11 Aug 2025

Top hotels in Hillside

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €252 per night from 7 Sept to 8 Sept
€252
7 Sept - 8 Sept
includes taxes & fees
7.8/10 Good! (8,939 reviews)
Vintage hotel in amazing location
"This is a beautiful old hotel in a great location in very good to excellent condition. The A/C worked fine, the bed was comfortable, and we had a lovely view of the lake and the fireworks at Navy Pier. The location, right across from Buckingham Fountain, is great. My partner and I thought that the ..."

Reviewed on 10 Aug 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €196 per night from 4 Sept to 5 Sept
€196
4 Sept - 5 Sept
includes taxes & fees
8.4/10 Very Good! (1,849 reviews)
"5 star rating! The vibe of the hotel is amazing and you can’t beat the location."

Reviewed on 11 Aug 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €144 per night from 2 Sept to 3 Sept
€144
2 Sept - 3 Sept
includes taxes & fees
8.4/10 Very Good! (3,657 reviews)
"Great rooms, comfortable, walking distance to anywhere you’d want to go."

Reviewed on 10 Aug 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 5,072 properties in Hillside
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

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
Magnificent Mile - River North showing street scenes, signage and night scenes

Michigan Avenue

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Hillside

River tour boat in Chicago

Architecture River Tour

€36
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

€39
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
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 Hillside

Frequently asked questions

How much does a Hillside holiday package cost?
Offering excellent value package deals from €1,102 on Expedia, you'll be thrilled with how little a holiday to Hillside costs! Our packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Hillside?
You're likely to find lower rates and greater availability in December, January and February. Explore our cheap Hillside holiday packages and you could get some great off-season discounts.
How many days is enough for Hillside?
Typically, a handful of days is enough to check out the top attractions during your Hillside holiday. But if you'd like to have more time to rest or take day trips, consider extending your itinerary.
How to find the best Hillside package deals?
Landing a cheap Hillside package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to view the most affordable Hillside package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Hillside holiday as a package?
An Expedia holiday package could score you significant savings when compared to arranging hotels and flights separately. Better still, you can tailor your Hillside escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Hillside?
If you're considering an impromptu Hillside getaway, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Hillside?

  1. Choose your travel dates: What you'd like to do in Hillside and your favourite season can help you decide when to travel.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and dining out to activities and airfares. Your accommodation will likely be the biggest expense during your trip to Hillside.
  3. Decide how long to go away for: Now that you're more familiar with Hillside, you can figure out the perfect length of your break. Pull together a draft itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a tailored Hillside holiday package.

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