Highland Park Vacations
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Highland Park Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
$430
per person
Oct 22 - Oct 26
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Where to start…. 1. The “free” breakfast was absolutely awful. Some really big bowls full of cereal, some fruit and a lot of bread. Honestly, one of the worst breakfast buffet I have ever seen. 2. The AC went out in our room and it was over 87° all night. Horrible night sleep. They couldn’t help until the next morning. Yes, they gave us a new room… but why couldn’t they do that overnight. Location was great, but that’s the only plus.
Reviewed on Aug 12, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
$777
per person
Oct 22 - Oct 26
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
A very pretty hotel that is clean and has nice restaurants. The free breakfast buffet is unreal!
Reviewed on Aug 12, 2026
Swissotel - Chicago
Downtown Chicago
$805
per person
Oct 22 - Oct 26
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
$554
per person
Oct 22 - Oct 26
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Great service
Reviewed on Aug 11, 2026
The Talbott, Autograph Collection
Downtown Chicago
$609
per person
Oct 22 - Oct 26
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
$753
per person
Oct 22 - Oct 26
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
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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 ...
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 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 ...
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 ...
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 ...
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. ...
The Majestic Hotel
528 W Brompton Ave Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and a fireplace in the lobby. Our guests praise the helpful staff and the ...
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.
Thu, Aug 13 - Tue, Sep 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$176
Roundtrip
found 1 day ago
Tue, Sep 1 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$195
Roundtrip
found 9 hours ago
Tue, Oct 20 - Sat, Nov 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$195
Roundtrip
found 9 hours ago
Tue, Sep 1 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$195
Roundtrip
found 9 hours ago
Tue, Sep 1 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$313
Roundtrip
found 9 hours ago
Best points of interest in Chicago
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All accommodation types in Highland Park
More Types of Hotels
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- Smoke Free Hotels in Highland Park
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- Hotel with wifi in Highland Park
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- Family Hotels in Highland Park