Highland Hills Vacation Packages
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Your Highland Hills Vacation
Get ready to experience Highland Hills in your own style with a custom Highland Hills vacation package! Uncovering the best parts of this fascinating city is made easier with a base in a neighborhood such as Clarendon Hills, which is good for golfing, among plenty of other things. Yorktown Shopping Center and Lilacia Park are some of the major attractions to tour during a trip to Highland Hills. Expedia is here to help you escape your routine. Tailor your vacation to Highland Hills to suit your travel style, whatever that may be.
Price found within the past 48 hours. Click for updated prices.
- The Talbott, Autograph Collection
Jun 27 - Jul 1The Talbott, Autograph Collection + Flight
Downtown Chicago4 nights9.4/10 - Exceptional (116 reviews)"We thoroughly enjoyed our stay. The location was excellent, conveniently close to everything we needed. The room was spacious and spotless. The breakfast was fantastic, offering a wide variety of options to choose from. "Reviewed May 17, 2026Roundtrip • Toronto (YTZ) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YTZ • NonstopCA $1,550CA $1,032found 1 day agoper traveller - Level Chicago – Old Town
Aug 2 - Aug 7Level Chicago – Old Town + Flight
Downtown Chicago5 nights9.0/10 - Wonderful (480 reviews)"Super nice"Reviewed May 20, 2026Roundtrip • Hamilton (YHM) - Chicago (ORD)YHM - ORD • 1 stop ORD - YYZ • 1 stopCA $2,232CA $1,411found 14 hours agoper traveller - Pendry Chicago
Jul 9 - Jul 12Pendry Chicago + Flight
Downtown Chicago3 nights9.2/10 - Wonderful (1,116 reviews)"Great staff and perfect place to be in the middle of everything!"Reviewed April 27, 2026Roundtrip • Toronto (YTZ) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YYZ • NonstopCA $1,614CA $1,097found 9 hours agoper traveller - Level Chicago Fulton Market
Jul 28 - Aug 1Level Chicago Fulton Market + Flight
Downtown Chicago4 nights9.2/10 - Wonderful (488 reviews)"Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely."Reviewed May 22, 2026Roundtrip • Edmonton (YEG) - Chicago (ORD)YEG - ORD • 1 stop ORD - YEG • 1 stopCA $2,437CA $1,661found 1 day agoper traveller - Swissotel - Chicago
Aug 8 - Aug 12Swissotel - Chicago + Flight
Downtown Chicago4 nights9.0/10 - Wonderful (3,337 reviews)"Great location!"Reviewed May 23, 2026Roundtrip • Edmonton (YEG) - Chicago (ORD)YEG - ORD • Nonstop ORD - YEG • NonstopCA $1,801CA $1,286found 1 day agoper traveller
Where to stay in Highland Hills
Find the best Highland Hills areas and neighborhoods for the activities you enjoy most. Learn more about Highland Hills
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Highland Hills Hotel Deals
SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street Lombard IL
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Jun 7 to Jun 8
CA $128
CA $142 total
Jun 7 - Jun 8
includes taxes & fees
9/10 Wonderful! (2,755 reviews)
"Checking in was easy and room was semi clean. The blanket in the closet was covered in food and super dirty. Saw a sign that said water maintenance would be over at 12pm. Checked in at 3pm, water still didn't work until 4pm. It was very inconvenient."
Reviewed on May 22, 2026
Holiday Inn Chicago Dwtn - The Mart by IHG
350 West Wolf Point Plaza, Building 2 Chicago IL
The price is CA $261 per night from May 26 to May 27
CA $261
CA $311 total
May 26 - May 27
includes taxes & fees
8.8/10 Excellent! (2,325 reviews)
"The location is very good, but the hotel needs to make some improvements. First, when you enter, there is a strong smell of humidity, which I imagine is coming from the carpet. The same smell was noticeable in the hallways and in the room. In the room, I found that the sink was clogged, and the shower ..."
Reviewed on May 21, 2026
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street Chicago IL
Fully refundable
The price is CA $234 per night from May 26 to May 27
CA $234
CA $278 total
May 26 - May 27
includes taxes & fees
9/10 Wonderful! (2,207 reviews)
"All of the staff were incredibly nice!"
Reviewed on May 24, 2026
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.
Frequently asked questions
Discover the most popular places to visit in Highland Hills
Wrigley Field
4.5/5(159 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
4.5/5(3 reviews)
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Navy Pier
4.5/5(460 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Skydeck - Willis Tower Admission
CA $60
per adult
96% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.