Highwood Holiday Rentals, Chicago: Private House Rentals

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Our top choices for Highwood hotels

A spacious lobby with a reception desk, seating area, and a large glass door entrance.

A hotel room with a large bed, a desk, a chair, a television, and a sofa.

A spacious dining area with multiple tables and chairs, large windows, and a central decorative plant.

A large indoor swimming pool with multiple lounge chairs and a blue chair in the center.

1. La Quinta Inn & Suites by Wyndham Bannockburn-Deerfield

Deerfield

Elvia

฿2,798

฿3,105 total

includes taxes & fees

4 Oct - 5 Oct

A Courtyard by Marriott hotel with a well-lit entrance, landscaped surroundings, and a modern architectural design.

A modern living room with a fireplace, comfortable seating, and large windows.

A pool area with a glass-enclosed patio, furnished seating, and a clear view of the surrounding buildings.

A modern bar area with a bar counter, seating, and a menu board.

2. Courtyard by Marriott Chicago Highland Park/Northbrook

Highland Park

Michael

฿3,818

฿4,238 total

includes taxes & fees

20 Sept - 21 Sept

A spacious lobby with a central seating area, a piano, and a large window overlooking a garden.

A hotel corridor with multiple tables and decorative vases, featuring a modern chandelier and framed artwork on the walls.

A spacious dining area with multiple tables, chairs, and a central fireplace.

A conference room with rows of chairs facing a large screen, a podium, and a blue-lit ceiling.

3. Hyatt Regency Deerfield

Deerfield

Maria

฿4,169

฿4,710 total

includes taxes & fees

7 Sept - 8 Sept

An outdoor patio with a wooden table and chairs, a stone wall, and a grill.

A reception area with a glass door, a bench, a lamp, and a wall with a stone pattern.

A modern restaurant with green seating, multiple tables, and pendant lighting.

A hotel room with a sofa, a bed, a desk, a chair, and a television.

4. Home2 Suites by Hilton Lincolnshire Chicago

Lincolnshire

Michael

฿4,022

฿4,504 total

includes taxes & fees

11 Sept - 12 Sept

A modern restaurant with a bar area, a large dining table with chairs, and a fireplace.

A snack and beverage section with shelves stocked with chips, snacks, and drinks.

A modern lounge area with leather sofas, armchairs, and a fireplace.

A swimming pool with clear water, surrounded by lounge chairs and tables, large windows with a view of trees and buildings, and a ceiling with recessed lighting.

5. Hampton Inn & Suites Chicago/Lincolnshire

Lincolnshire

Samantha

฿3,212

฿3,597 total

includes taxes & fees

2 Oct - 3 Oct

A spacious lobby with a central reception area, a shop, and potted plants.

An indoor swimming pool with clear windows, chairs, and potted plants.

A modern building with a curved glass facade, a water feature in front, and a landscaped area with shrubs.

A spacious dining area with long tables and chairs, a reception desk, and a bar area.

6. Hilton Garden Inn Lake Forest Mettawa

Lake Forest

Spencer

฿4,562

฿5,063 total

includes taxes & fees

11 Sept - 12 Sept

A Holiday Inn Express & Suites building with a covered entrance, stone pillars, and a clear blue sky.

A reception desk with a modern design, featuring a glass panel with the hotel's name and a digital screen. There are two receptionists' stations with computers and a small coffee machine.

A gym with treadmills, exercise bikes, and a mirrored wall.

A hotel room with a bed, a nightstand, a lamp, and a sofa.

7. Holiday Inn Express & Suites Prospect Heights by IHG

Prospect Heights

Silver

฿3,950

฿4,423 total

includes taxes & fees

20 Sept - 21 Sept

Staybridge Suites hotel with a stone facade, a covered entrance, and a sign above the entrance.

A swimming pool with clear blue water, a diving board, and a lifeguard stand.

A garden with a gazebo, various flower beds, and a brick pathway.

A compact kitchen with dark cabinets, a white refrigerator, a coffee maker, and a dining area with striped chairs.

8. Staybridge Suites Chicago - Glenview by IHG

Glenview

Kenneth

฿4,115

฿4,649 total

includes taxes & fees

27 Sept - 28 Sept

A spacious lobby with a high ceiling, a large abstract painting, a dining area, and a staircase leading to an upper level.

An indoor garden with tables and chairs, a large wall with a quote, and hanging spherical lights.

An indoor swimming pool with lounge chairs and a table, surrounded by potted plants and a large window with a view.

9. Renaissance Chicago Glenview Suites Hotel

Glenview

Jorge

฿3,924

฿4,433 total

includes taxes & fees

20 Sept - 21 Sept

A hotel room with a large bed, a bedside table with a lamp, a wall-mounted phone, and a built-in shelf.

A modern living room with grey upholstered armchairs, a round coffee table, and a flat-screen TV above a fireplace.

A hotel room with a sofa, a small coffee table, a desk with a chair, a flat-screen TV mounted on the wall, and a kitchenette in the background.

A reception area with a stone counter, a map on the wall, and a seating area with a sofa and armchairs.

10. Best Western Glenview -Chicagoland Inn and Suites

Glenview

Ermir

฿3,078

฿3,477 total

includes taxes & fees

7 Sept - 8 Sept

A multi-story hotel with a prominent "Hyatt Place" sign, a well-lit entrance, and a landscaped front yard.

A banquet hall with round tables set for a formal event, featuring floral centerpieces and elegant table settings.

A modern kitchen with white cabinets, a central island with beverages, and pendant lighting.

A modern bar area with a counter, seating, and a patterned wall.

11. Hyatt Place Chicago/O'Hare Airport

Rosemont

Lynetta

฿4,740

฿5,403 total

includes taxes & fees

21 Sept - 22 Sept

A modern hotel room with a red sofa, a red ottoman, a large mirror, and a painting of a building on the wall.

A hotel with a large building, a fountain, and a pond.

A reception area with a large digital display, a seating area with a bench, and a reception desk.

A hotel lobby with a reception desk, seating area, and a dining section.

12. Hotel Indigo Chicago-Vernon Hills by IHG

Vernon Hills

Alfredo

฿3,753

฿4,165 total

includes taxes & fees

13 Sept - 14 Sept

A hotel lobby with a staircase, seating area, and a reception desk.

A hotel room with two beds, green walls, framed pictures, a bedside table, and a window with blinds.

A hotel room with two armchairs, a sofa, a coffee table, a lamp, a mirror, and a window with curtains.

A breakfast bar with coffee machines, a fruit display, and a dining area with wooden chairs and a table.

13. Sleep Inn near Great Lakes Naval Base

North Chicago

Sheyla

฿2,938

฿3,393 total

includes taxes & fees

27 Sept - 28 Sept

A modern hotel lobby with a bar area, seating arrangements, and a large abstract artwork on the wall.

A hotel reception desk with a red wall displaying "WELCOME TO THE PRAIRIE STATE" and a sign for Hilton Honors.

An indoor swimming pool with clear blue water, surrounded by chairs and a lifeguard stand.

An outdoor patio with seating arrangements, including tables and chairs, and large umbrellas providing shade.

14. Hampton Inn & Suites Chicago Waukegan

Waukegan

Chanda

฿3,077

฿3,446 total

includes taxes & fees

13 Sept - 14 Sept

A modern hotel lobby with round tables, blue upholstered chairs, and large windows offering a view of the outdoors.

An indoor swimming pool with clear windows, green chairs, and a tiled deck.

A Hampton Inn hotel with a modern facade, large windows, and a welcoming entrance.

A hotel room with two beds, a desk, a chair, a TV, and a window with a view.

15. Hampton Inn Chicago-O'Hare International Airport

Schiller Park

Jean

฿3,259

฿3,747 total

includes taxes & fees

7 Sept - 8 Sept

A bar area with wooden bar counter, metal chairs, and a variety of bottles and glasses.

An indoor swimming pool with clear water, surrounded by lounge chairs and a glass wall.

A modern living room with a stone wall, a flat-screen TV, a sofa, chairs, a coffee table, and decorative items.

A Fairfield by Marriott hotel with a modern design, featuring a prominent entrance, a covered walkway, and a landscaped area.

16. Fairfield Inn & Suites by Marriott Chicago O'Hare

Des Plaines

Jorge

฿5,303

฿6,044 total

includes taxes & fees

20 Sept - 21 Sept

A long, narrow hallway with a patterned carpet, recessed lighting, and doors on one side.

A modern interior with a wall-mounted fireplace, a rock installation, and a green wall.

A modern building entrance with a car parked in front.

A modern bar area with a curved ceiling, wooden slats, and a bar counter with stools.

17. Loews Chicago O'Hare Hotel

Rosemont

Patricia

฿7,867

฿8,967 total

includes taxes & fees

11 Sept - 12 Sept

An outdoor patio area with wicker furniture, a round fire pit, and a pergola structure.

A modern building with large glass windows, a covered walkway, and a reflective water body in front.

A hotel lobby with seating areas, a fireplace, and a bar.

A large, symmetrical building with a central entrance, flanked by two wings, and surrounded by well-maintained lawns and hedges.

18. Staybridge Suites, Lincolnshire by IHG

Half Day

Miguel

฿4,115

฿4,608 total

includes taxes & fees

8 Sept - 9 Sept

A modern building with a glass facade and a curved structure.

A reception area with a marble wall, multiple reception counters, and a modern design.

A woman running on a treadmill in a gym with another person in the background.

A conference room with a long table, purple chairs, and framed pictures on the walls.

19. Hyatt Regency O'Hare Chicago

Rosemont

Marisa

฿5,892

฿6,716 total

includes taxes & fees

7 Sept - 8 Sept

A modern lounge area with leather sofas, a coffee table, and a patterned rug.

A hotel room with two beds, a desk, a chair, a TV, and a large window with a city view.

An outdoor patio with a wooden table and wicker chairs, surrounded by blue umbrellas, and a building with large windows in the background.

A modern living room with a brown leather sofa, a coffee table, and a side table with a lamp.

20. Holiday Inn Chicago O'Hare – Rosemont by IHG

Rosemont

Bianca

฿4,674

฿5,385 total

includes taxes & fees

7 Sept - 8 Sept

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Top Highwood Hotel Reviews

DoubleTree by Hilton Chicago - North Shore Conference Center

10/10 Excellent

"The location is excellent, close to a variety of restaurants and shopping. I was using Uber/Lyft to get around, but could easily walk to nearby businesses and restaurants. This is an older property that has been nicely modernized and is well maintained. The floor mounted air conditioning unit was very quiet, even at high speed, and the wall mounted temperature control worked well. Because it is an older property it did not have a lot of plugins, but they were sufficient. I appreciated the low slung dresser which had ample storage, and there was a room safe. The location is not near a highway and the room was quiet at night. The TV quality was good. My only wish, which applies to almost all hotels these days, is that I wish there was more than one hook in the room."

Embassy Suites by Hilton Chicago O'Hare Rosemont

10/10 Excellent

"Convenient location, clean rooms, good food, al Good"

Hyatt Place Chicago/O'Hare Airport

8/10 Good

"Room was fine Air con was noisy, shower was great location good. Breakfast was a letdown in terms of quality"

Hyatt Regency O'Hare Chicago

10/10 Excellent

"Had a quiet and productive weekend. Will definitely stay here again. Thanks"

DoubleTree by Hilton Chicago O'Hare Airport - Rosemont

10/10 Excellent

"The front desk staff was extremely helpful and friendly. Nice large shower."

Comfort Suites Chicago O'Hare Airport

10/10 Excellent

"All around, great stay!"

Holiday Inn Chicago North-Evanston by IHG

10/10 Excellent

"We felt the Holiday Inn was quite the bang for the buck. Close enough to the train stations to be convenient, but not so far out of the city to take a long time. Access to Chicago proper was very easy, and there were a lot of good and reasonably priced restaurants in the Evanston area. Rooms are comfortable & reasonably clean"

SpringHill Suites Chicago O'Hare by Marriott

10/10 Excellent

"Great room large size. Comfortable bed and pillows. Great breakfast in the morning."

More cheap stays in Highwood

Motel 6 Prospect Heights, IL

540 N Milwaukee Ave Prospect Heights IL

฿1,738

฿1,946 total

22 Sept - 23 Sept

includes taxes & fees

Motel 6 Elk Grove Village, IL - O'Hare

2881 Touhy Ave Elk Grove Village IL

฿1,738

฿1,963 total

1 Oct - 2 Oct

includes taxes & fees

Motel 6 Schiller Park, IL - Chicago O'Hare

9408 Lawrence Avenue Schiller Park IL

฿1,883

฿2,165 total

21 Sept - 22 Sept

includes taxes & fees

6.8/10 (2,334 reviews)

Quality Inn O'Hare Airport

3801 North Mannheim Road Schiller Park IL

฿2,871

฿3,301 total

27 Sept - 28 Sept

includes taxes & fees

Hampton Inn Chicago-O'Hare International Airport

3939 N Mannheim Rd Schiller Park IL

฿3,259

฿3,747 total

7 Sept - 8 Sept

includes taxes & fees

9.2/10 Wonderful! (2,392 reviews)

Sonesta Simply Suites Chicago O'Hare Airport

4021 North Mannheim Rd Schiller Park IL

฿3,818

฿4,390 total

23 Sept - 24 Sept

includes taxes & fees

Frequently asked questions

What's the best place for a stay in Highwood?

Hyatt Regency O'Hare Chicago, located 15.8 mi (25.4 km) from the heart of Highwood, is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Hilton Chicago O'Hare Airport and Holiday Inn Chicago O'Hare – Rosemont by IHG. See all available top hotels, or vacation rentals in Highwood.

If I need to cancel my hotel reservation in Highwood, will I receive a refund?

Yes! Most hotel bookings are refundable provided that you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel and be given a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Highwood.

What are some accommodation options with pools in Highwood?

Holiday Inn Chicago O'Hare – Rosemont by IHG: Hotel, 7-minute walk from Allstate Arena. Provides complimentary wireless Internet access, an indoor pool and Smart televisions. Embassy Suites by Hilton Chicago O'Hare Rosemont and Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG are a couple of other choices with an on-site pool. View all hotels with pools in Highwood.

How is it to stay in Highwood?

Visitors can enjoy all that Highwood has to offer, including the shopping and restaurants. A top sight in the area is Six Flags Great America. In Highwood, there are 11 hotels and other accommodation options to choose from. Find out more about Highwood.

What should I do while I'm visiting Highwood?

Six Flags Great America is a notable place to visit in the area. You'll also find Ravinia Pavilion and Chicago Botanic Garden in the area. Take a look at what more there is to see and do in Expedia's Highwood guide.

What's the best way to get around Highwood?

To see more of the surrounding area, ride one of the trains from Highwood Station or Highland Park Fort Sheridan Station. If you want to venture out around the area, you may want a rental car in Highwood for your journey.

What's the seasonal weather in Highwood?

The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of -1°C. Average annual precipitation for Highwood is 1183 mm.

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Book Hotels in Highwood on Expedia.com

Find hotels in Highwood, IL from ฿1,946

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Highwood

Check prices for these dates

Filter by

Star rating

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Our top choices for Highwood hotels

1. La Quinta Inn & Suites by Wyndham Bannockburn-Deerfield

2. Courtyard by Marriott Chicago Highland Park/Northbrook

3. Hyatt Regency Deerfield

4. Home2 Suites by Hilton Lincolnshire Chicago

5. Hampton Inn & Suites Chicago/Lincolnshire

6. Hilton Garden Inn Lake Forest Mettawa

7. Holiday Inn Express & Suites Prospect Heights by IHG

8. Staybridge Suites Chicago - Glenview by IHG

9. Renaissance Chicago Glenview Suites Hotel

10. Best Western Glenview -Chicagoland Inn and Suites

11. Hyatt Place Chicago/O'Hare Airport

12. Hotel Indigo Chicago-Vernon Hills by IHG

13. Sleep Inn near Great Lakes Naval Base

14. Hampton Inn & Suites Chicago Waukegan

15. Hampton Inn Chicago-O'Hare International Airport

16. Fairfield Inn & Suites by Marriott Chicago O'Hare

17. Loews Chicago O'Hare Hotel

18. Staybridge Suites, Lincolnshire by IHG

19. Hyatt Regency O'Hare Chicago

20. Holiday Inn Chicago O'Hare – Rosemont by IHG

Learn more about Highwood

Top Highwood Hotel Reviews

DoubleTree by Hilton Chicago - North Shore Conference Center

Embassy Suites by Hilton Chicago O'Hare Rosemont

Hyatt Place Chicago/O'Hare Airport

Hyatt Regency O'Hare Chicago

DoubleTree by Hilton Chicago O'Hare Airport - Rosemont

Comfort Suites Chicago O'Hare Airport

Holiday Inn Chicago North-Evanston by IHG

SpringHill Suites Chicago O'Hare by Marriott

More cheap stays in Highwood

Motel 6 Prospect Heights, IL

Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Schiller Park, IL - Chicago O'Hare

Quality Inn O'Hare Airport

Hampton Inn Chicago-O'Hare International Airport

Sonesta Simply Suites Chicago O'Hare Airport

Frequently asked questions

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