Highland Park Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Highland Park Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$458
per person
Oct 26 - Oct 30
found 14 hours ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Great staff, very clean property. Enjoyed the café for lattes and cocktails! Breakfast is a fair price for being additional. I loved the location many bars and restaurants just a few minutes walk away.
Reviewed on Aug 19, 2026
Level Chicago Fulton Market
Downtown Chicago
$776
per person
Oct 26 - Oct 30
found 14 hours ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.
Reviewed on Aug 17, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
$666
per person
Oct 26 - Oct 30
found 14 hours ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Good overall
Reviewed on Aug 20, 2026
Level Chicago – Old Town
Downtown Chicago
$595
per person
Oct 26 - Oct 30
found 14 hours ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Beautiful property in great location! Would have definitely been a 5 but rooms facing the pool was very noisy
Reviewed on Aug 19, 2026
The Talbott, Autograph Collection
Downtown Chicago
$593
per person
Oct 26 - Oct 30
found 14 hours ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Front desk manager agreed to change my date with on-line service from the next weekend to the current weekend, so I booked and checked in.
4 days later, the on-line booking co. Said the manager did not agree to release my reservation.
Unethical procedurers.
Reviewed on Aug 12, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
$494
per person
Oct 26 - Oct 30
found 14 hours ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Nothing unique
Reviewed on Aug 20, 2026
Don't see what you're looking for?
See all available trips from Columbus to Highland Park
View all tripsHighland Park Vacation Packages
Trying to plan a way to package your Highland Park flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® can help you get everything you need, while saving you both money and some time. We're here to book everything you'll need to make your Highland Park trip one to remember. In only a few clicks, you can select the best vacation package for you. AARP Travel Center has an incredible selection of flights and lodgings, as well as Highland Park activities to pull from.
Hotels in Highland Park
Our listings include hotels that are close to all the Highland Park points of interest, and some that are just outside the city center for a quieter retreat.
From Highland Park hotels with swimming pools and on-site restaurants, to boutique accommodations that add all the thoughtful touches, you'll get a hotel here that will make your trip amazing. With AARP Travel Center's Highland Park hotel packages, you not only get a great rate on your flight, but also a fantastic place to stay.
Things to do in Highland Park
Highland Park has about 29,743 people that call this city their home. If you wanted to take a break from the bustle of a big city, then you chose the perfect place. With Highland Park's burgeoning artistic community and plenty of interest for history buffs you may have a hard time fitting everything into one trip.
The AARP Travel Center "Things to Do" page has more great activities that you can book.
Package Your Highland Park Vacation and Save
With so much to see and do in Highland Park, you'll be wanting to plan your outings, not devoting time to searching for the hotel with the lowest rate. AARP Travel Center allows you to quickly book everything you need, and save some cash on your vacation. You can plan your whole holiday, including things to do in Highland Park from only one place. So what are you waiting for? Book today and save!
Top Hotel Deals
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
Holiday Inn Chicago O'Hare – Rosemont by IHG
6600 Mannheim Road, building 2 Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast ...
Comfort Suites Chicago O'Hare Airport
4200 North River Road Schiller Park IL
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
Loews Chicago O'Hare Hotel
5300 N River Rd Rosemont IL
Book a stay at this luxury hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful ...
Embassy Suites by Hilton Chicago O'Hare Rosemont
5500 N River Rd Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free breakfast, a free airport shuttle, and room service. Our guests praise the breakfast and ...
Hyatt Regency Deerfield
1750 Lake Cook Rd Deerfield IL
Book a stay at this business-friendly hotel in Deerfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
The Chicago Hotel Collection River North
312 W. Chestnut St. Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
DoubleTree by Hilton Chicago O'Hare Airport - Rosemont
5460 North River Road Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff ...
Super 8 by Wyndham Chicago O'Hare Airport
2951 Touhy Ave Elk Grove Village IL
Book a stay at this business-friendly hotel in Elk Grove Village. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
Holiday Inn Chicago O'Hare Area by IHG
5615 North Cumberland Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
Holiday Inn Chicago North-Evanston by IHG
1501 Sherman Ave Evanston IL
Book a stay at this business-friendly hotel in Evanston. Enjoy free WiFi, room service, and a fitness center. Our guests praise the breakfast and the helpful ...
Marriott Chicago O'Hare
8535 West Higgins Road Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a free airport shuttle, and a 24-hour fitness center. Our guests praise ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed, Oct 21 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$148
Roundtrip
found 8 hours ago
Tue, Oct 13 - Tue, Oct 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$173
Roundtrip
found 8 hours ago
Thu, Oct 1 - Mon, Oct 5
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197
Roundtrip
found 4 days ago
Sat, Oct 24 - Sat, Oct 31
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197
Roundtrip
found 7 hours ago
Fri, Oct 2 - Mon, Oct 5
LAX
Los Angeles Intl.
MDW
Midway Intl.
$207
Roundtrip
found 15 hours ago
Best points of interest in Chicago
More AARP Member Vacation Packages
- Las Vegas Vacations
- New York Vacations
- Orlando Vacations
- Los Angeles Vacations
- Miami Vacations
- San Francisco Vacations
- New Orleans Vacations
- Chicago Vacations
- Fort Lauderdale Vacations
- Boston Vacations
- Honolulu Vacations
- San Diego Vacations
- Washington Vacations
- Toronto Vacations
- Anaheim Vacations
- Atlanta Vacations
- Nashville Vacations
- Seattle Vacations
- Phoenix Vacations
- Myrtle Beach Vacations
- Vancouver Vacations
- Palm Springs Vacations
- Denver Vacations
- Tampa Vacations
- Niagara Falls Vacations
- San Antonio Vacations
- Atlantic City Vacations
- Philadelphia Vacations
- Austin Vacations
- Dallas Vacations
All accommodation types in Highland Park
More Types of Hotels
- Hotels with Balconies in Highland Park
- Hotels with Bars in Highland Park
- Hotels with WiFi in Highland Park
- Hotels with a Pool in Highland Park
- Hotels with Hot Tubs in Highland Park
- Lakefront Hotels in Highland Park
- Smoke Free Hotels in Highland Park
- Hotels with an Indoor Pool in Highland Park
- Hotel with wifi in Highland Park
- Hotels with Air Conditioning in Highland Park
- Beach Hotels in Highland Park
- Family Hotels in Highland Park