Highland Hills Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Highland Hills Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,241, price is now $833 per person
$833
per person
Sep 17 - Sep 21
found 6 hours ago
Roundtrip flight included
Columbia (CAE) 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 place!
Reviewed on Jul 2, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,646, price is now $975 per person
$975
per person
Sep 17 - Sep 21
found 6 hours ago
Roundtrip flight included
Columbia (CAE) 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.
The hotel is perfectly located near major tourist attractions, restaurants, and shops—all within easy walking distance. The rooms are clean, spacious, and equipped with all the essential amenities. The only downside is the lack of on-site parking; guests must park across the street for $55 per day.
Reviewed on Jul 2, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,779, price is now $1,143 per person
$1,143
per person
Sep 17 - Sep 21
found 6 hours ago
Roundtrip flight included
Columbia (CAE) 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.
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,721, price is now $1,154 per person
$1,154
per person
Sep 17 - Sep 21
found 6 hours ago
Roundtrip flight included
Columbia (CAE) 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.
Excellente
Reviewed on Jul 1, 2026
Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,301, price is now $924 per person
$924
per person
Sep 17 - Sep 21
found 6 hours ago
Roundtrip flight included
Columbia (CAE) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 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.
No one answers the phone at the spa.
Bathtub clogged, engineering called and I was simply told the tub was not clogged so had to shower with water up to my ankles.
They do have a bar but it’s not well stocked.
The blinds in the room don’t hang properly, they’re wonky, and have to be moved by chain.
This is not a 4 star hotel. It’s not 3 either. Save your money and stay at a nice Hampton or Courtyard instead. This is a gross place, terrible staff.
Reviewed on Jul 2, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,543, price is now $1,104 per person
$1,104
per person
Sep 17 - Sep 21
found 6 hours ago
Roundtrip flight included
Columbia (CAE) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
An amazing hotel with an amazing river view! I will definitely be staying there again!
Reviewed on Jul 1, 2026
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See all available trips from Columbus to Highland Hills
View all tripsHighland Hills Vacation Packages
Looking to save time and money on your upcoming holiday to Highland Hills? Don't worry, as AARP Travel Center Powered by Expedia® is here to help. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Highland Hills the best one yet. In only a few clicks, you can select the best Highland Hills vacation package for you. AARP Travel Center has a fabulous selection of flights and lodgings, as well as Highland Hills endeavors to pick from.
Hotel Deals in Highland Hills
Our listings include accommodations that are close to all the Highland Hills points of interest, and some that are just outside the city center for a quieter retreat.
We have great deals on everything from all-inclusive resorts that meet all the vacation must-haves to affordable hotels perfect for those on a budget. You can look through our vast catalog of options and choose the lodging that is perfect for you and your family. With AARP Travel Center's Highland Hills hotel packages, you not only get a great rate on your flight, but also a terrific place to stay.
Things to do in Highland Hills
You'll discover that Highland Hills typically has something to see and do. A little curiosity and asking the right people, like your hotel's concierge, goes a long way into having a unique experience.
If you need more suggestions, then make sure to click on AARP's "Things to Do" page.
Package Your Highland Hills Vacation and Save
As an AARP Member, you get to take advantage of all the great deals. You'll save on select hotels worldwide, flights, and also rental cars. No matter what Highland Hills vacation bundle you pick, your membership savings helps you get a great deal. So what are you waiting for? Book now and get ready for your Highland Hills vacation.
Top Hotel Deals
SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street Lombard IL
0.97 km from Highland Hills
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
18.49 km from Highland Hills
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 ...
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
16.05 km from Highland Hills
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 ...
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street Chicago IL
29.56 km from Highland Hills
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
Holiday Inn Chicago Dwtn - The Mart by IHG
350 West Wolf Point Plaza, Building 2 Chicago IL
30.38 km from Highland Hills
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street Chicago IL
30.09 km from Highland Hills
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
Marriott Chicago O'Hare
8535 West Higgins Road Chicago IL
19.85 km from Highland Hills
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 ...
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
24.02 km from Highland Hills
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd Rosemont IL
17.93 km from Highland Hills
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 ...
Comfort Suites Chicago O'Hare Airport
4200 North River Road Schiller Park IL
16.38 km from Highland Hills
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 ...
Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
6.22 km from Highland Hills
Book a stay at this business-friendly hotel in Westmont. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the clean rooms ...
Holiday Inn Chicago O'Hare – Rosemont by IHG
6600 Mannheim Road, building 2 Rosemont IL
18.93 km from Highland Hills
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 ...
Embassy Suites by Hilton Chicago O'Hare Rosemont
5500 N River Rd Rosemont IL
18.13 km from Highland Hills
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 ...
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, Aug 19 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$198 Roundtrip, found 1 day ago
$198
Roundtrip
found 1 day ago
Tue, Sep 1 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$238 Roundtrip, just found
$238
Roundtrip
just found
Tue, Sep 1 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$248 Roundtrip, just found
$248
Roundtrip
just found
Wed, Aug 12 - Tue, Sep 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$276 Roundtrip, found 5 days ago
$276
Roundtrip
found 5 days ago
Tue, Sep 1 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$277 Roundtrip, just found
$277
Roundtrip
just found