Deals on vacations and trips to Hillside

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Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Save 100% on your flight
Price was $432, price is now $248 per person
$248
per person
Dec 9 - Dec 13
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free full breakfast each morning.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $515, price is now $250 per person
$250
per person
Dec 9 - Dec 13
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 15 conference rooms on site, along with the valet parking and WiFi in public areas. Self parking, a lobby fireplace, and luggage storage are also offered.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $518, price is now $283 per person
$283
per person
Dec 9 - Dec 13
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $490, price is now $300 per person
$300
per person
Dec 9 - Dec 13
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, conference space, and valet parking. WiFi in public areas, luggage storage, and concierge services are also on offer.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,073, price is now $661 per person
$661
per person
Nov 21 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

Top Hillside hotels deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$152 nightly
The price is $179 total per night
$179 total
Oct 26 - Oct 27
Total with taxes and fees
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$131 nightly
The price is $154 total per night
$154 total
Oct 28 - Oct 29
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a coffee shop, and a snack bar/deli are also offered.
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$161 nightly
The price is $189 total per night
$189 total
Oct 20 - Oct 21
Total with taxes and fees
A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.
Pet friendly
Free WiFi
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$204 nightly
The price is $239 total per night
$239 total
Sep 28 - Sep 29
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, a communal living room, and express check-in are also on offer.
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$187 nightly
The price is $220 total per night
$220 total
Oct 1 - Oct 2
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. Express check-out, luggage storage, and concierge services are also on offer.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$226 nightly
The price is $266 total per night
$266 total
Oct 4 - Oct 5
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 15 conference rooms on site, along with the valet parking and WiFi in public areas. Self parking, a lobby fireplace, and luggage storage are also offered.
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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 cbd, a sporting event and a city

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 night scenes, a city and signage

Michigan Avenue

You can enjoy some retail therapy 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 featuring a sunset and rides

Navy Pier

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

Navy Pier

Frequently asked questions

How much are vacation packages to Hillside?
Your travel fantasies can become a reality in Hillside from an impressive $248. Vacation packages include flights and hotels, so organizing everything should be nice and easy. The only thing you'll need to concentrate on is getting out there and having a great time.
How long should my Hillside vacation be?
Most people spend roughly 2 nights in Hillside, but it's your call. If you want to venture out and explore all the amazing things this place has to offer, why not hang around another couple of nights?
Where can I get the best vacation package deals for Hillside?
There's no need to look any further than Travelocity. With as many as 400 airlines and 1,000,000 properties around the world, it's easy to find a Hillside package deal that suits your needs.
Why should I purchase my Hillside vacation package with Travelocity?
We make traveling the world easy. Whether you're seeking an amazing new place to uncover or want to ensure you get the best price on offer, we've got your back. Our 24/7 support, top-quality service and Price Match Guarantee mean you can confidently book with Travelocity.
Can I save money on my Hillside car rental if I book it with my hotel or flight?
Combining your car, hotel and flight into a Hillside vacation package is the easiest way to land the best deal. Plus, having your own car rental gives you freedom to get to all those amazing sights you'd like to check out. Situated 35 mi from Hillside, Six Flags Great America is one place that should feature on your itinerary. Put together a driving playlist and make a day trip of it.
Which airport is best for Hillside?
O'Hare Intl. Airport (ORD) is one of the biggest airports in Hillside. It's located 7 mi north of the city center. Your other options are Midway Intl. Airport (MDW) (10 mi away from central Hillside) and Lewis University Airport (LOT) (20 mi away from central Hillside).
What is there to do in Hillside?
Enjoy some great photo-ops at Fresh Meadow Golf Club, one of the most renowned attractions in Hillside. There's a lot more to discover in this exciting destination, so give yourself enough time to visit some of its off-the-beaten-path gems.
Where should I stay when visiting Hillside?
Many travelers opt to check in to the Holiday Inn Express & Suites Chicago West - OHare Arpt Area. It's a great base for your Hillside getaway.

Photos of local treasures

Browse Hillside vacation photos for more inspiration

Photo by Off The Beaten Track
Photo by Off The Beaten Track
Photo by Joe Farmer
Photo by Joe Farmer
Photo by Joe Farmer
Photo by Joe Farmer