Highland Hills Travel Guide

Chicago

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.

Wrigley Field
Magnificent Mile - River North which includes 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

With a visit to Navy Pier, a favourite shopping spot in Chicago, you can search for that perfect souvenir. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Navy Pier
McCormick Place

McCormick Place

During your trip, find out what's happening in McCormick Place, a top convention centre in Chicago. Discover the fascinating museums and notable monuments in this vibrant area.

McCormick Place
Millennium Park which includes autumn colours, modern architecture and street scenes

Millennium Park

After visiting Millennium Park, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the acclaimed art galleries in this vibrant area.

Millennium Park
Soldier Field which includes a high-rise building, a city and modern architecture

Soldier Field

Catch an event at Soldier Field during your trip to Chicago. Stroll along the lakeside or visit the notable monuments in this vibrant area.

Soldier Field

Top hotels in Highland Hills

SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

2.5 out of 5
222 E 22nd Street, Lombard, IL
The price is 1.882.802 ₫ per night from 16 Sept to 17 Sept
1.882.802 ₫
2.089.534 ₫ total
16 Sept - 17 Sept
includes taxes & fees
Stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
8.8/10 Excellent! (2,182 reviews)
"It was really nice. It smelled good and the rooms were nice as well"

Reviewed on 19 Aug 2025

SureStay Plus Hotel by Best Western Chicago Lombard
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
The price is 4.720.767 ₫ per night from 24 Aug to 25 Aug
4.720.767 ₫
5.541.758 ₫ total
24 Aug - 25 Aug
includes taxes & fees
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free Wi-Fi, breakfast (surcharge) and a fitness centre. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,392 reviews)
"Good experience with the staff"

Reviewed on 19 Aug 2025

Crowne Plaza Chicago West Loop by IHG
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport, Chicago, IL
The price is 4.727.360 ₫ per night from 19 Sept to 20 Sept
4.727.360 ₫
5.549.446 ₫ total
19 Sept - 20 Sept
includes taxes & fees
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge) and a free airport shuttle. Our guests praise the helpful ...
8.2/10 Very Good! (2,097 reviews)
"The room was clean and the bed was comfortable. The staff was courteous and helpful."

Reviewed on 18 Aug 2025

Hilton Chicago O'Hare Airport
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road, Chicago, IL
The price is 3.773.976 ₫ per night from 6 Sept to 7 Sept
3.773.976 ₫
4.430.271 ₫ total
6 Sept - 7 Sept
includes taxes & fees
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a free airport shuttle and a 24-hour fitness centre. Our guests praise ...
8.4/10 Very Good! (1,128 reviews)
"Room was grear & bed super comfortable"

Reviewed on 18 Aug 2025

Marriott Chicago O'Hare
DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville

4 out of 5
3003 Corporate West Dr, Naperville, IL
The price is 2.198.893 ₫ per night from 7 Sept to 8 Sept
2.198.893 ₫
2.440.332 ₫ total
7 Sept - 8 Sept
includes taxes & fees
Stay at this 4-star business-friendly hotel in Naperville. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (1,093 reviews)
"This was a horrible experience. The bedding was dirty and stained.. basically used. They provided a new room which smelled so bad we had to check out . The smell made my eyes & throat hurt and my daughter was getting a headache from the smell. We checked out and left the hotel. They said they would ..."

Reviewed on 19 Aug 2025

DoubleTree by Hilton Lisle Naperville
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
The price is 3.560.355 ₫ per night from 24 Aug to 25 Aug
3.560.355 ₫
4.058.093 ₫ total
24 Aug - 25 Aug
includes taxes & fees
Stay at this eco-certified hotel in Rosemont. Enjoy free Wi-Fi, breakfast (surcharge) and a free airport shuttle. Our guests praise the helpful staff and the ...
8.6/10 Excellent! (1,873 reviews)
"The staff was amazing, and made sure that we had access to a mini fridge for our daughter's insulin. The hotel was clean end organized- and that's hard during a convention. Can't beat the location, either!"

Reviewed on 21 Aug 2025

Hyatt Regency O'Hare Chicago
See all 3,079 properties in Highland Hills
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.

Other neighbourhoods around Highland Hills

Rosemont

O'Hare

3.5/5(10 area reviews)

Travellers choose O'Hare for its abundant dining options. Hop aboard the metro at Cumberland Station or Rosemont Station and check out top sights like Rosemont Theatre.

O'Hare
Default Image

Wicker Park

Spend some time visiting places like Milwaukee Avenue while getting to know Wicker Park, and be sure to check out the abundant dining options. You can hop aboard the metro at Damen Station or Division Station to see more of the area.

Wicker Park
Default Image

West Town

4.5/5(3 area reviews)

Noted for its live music and theatres, there's plenty to explore in West Town. Top attractions like The Salt Shed and Milwaukee Avenue are major draws, and you can hop on the metro at Division Station or Damen Station to see more of the city.

West Town
Default Image

Near West Side

4.5/5(14 area reviews)

Live music, theatres and shopping highlight some notable features of Near West Side. Make a stop by United Center or Credit Union 1 Arena while you're visiting, and jump aboard the metro at Racine Station or Polk Station (Pink Line) to get around town.

Near West Side
Default Image

West Loop

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.

West Loop
Default Image

Lakeview

4.5/5(8 area reviews)

Known for its lively bars and lake views, there's plenty to explore in Lakeview. Top attractions like Wrigley Field and Lake Michigan are major draws, and you can catch the metro at Southport Station or Addison Station (Red Line) to see more of the city.

Lakeview

Highland Hills Travel Guide

Choose two or more items and save on your trip: