Highland Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Highland 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 4 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 4 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 4 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.
Very pricey but then again its downtown Chicago. Excellent breakfast buffet, very roomy shower and entire bathroom. Comfortable bed, needs better pillows, very secure.
Reviewed on Aug 20, 2026
Level Chicago – Old Town
Downtown Chicago
$595
per person
Oct 26 - Oct 30
found 4 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 4 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 4 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.
Very nice place to stay. Rooms were just a bit on the smaller side.
Reviewed on Aug 19, 2026
Highland Vacation Packages
Hoping to save time and money on your upcoming vacation to Highland? The AARP Travel Center Powered by Expedia® can help you do both. We're here to book everything you'll need to make your Highland trip one to remember. With just a few clicks, you can pick the best vacation package for you. We have an amazing choice of flights and lodgings, as well as Highland activities to pull from.
Highland Hotel Deals
Our listings include hotels that are close to all the Highland points of interest, and some that are just outside the city center for a peaceful retreat.
From Highland hotels with pools and on-site restaurants, to boutique accommodations that add all the thoughtful touches, you'll find a hotel here that will make your trip one to remember. With AARP Travel Center's Highland hotel packages, you not only get a great rate on your flight, but also a terrific place to stay.
Things to do in Highland
Highland has about 22,936 people that make this city their home. If you needed a break from the bustle of a big city, then you picked the right town. With Highland's growing artistry scene and a rich past that is a beacon for history enthusiasts you may have a hard time fitting everything into one trip.
Looking for more? Then Check out AARP Travel Center's "Things to Do" Page.
Save with a Highland Vacation Package
As an AARP Member, you can take advantage of all the great deals. You can save on select hotels worldwide, flights, and rental cars. No matter what vacation package you select, you can rest easy knowing that you already saved on your trip. So what are you waiting for? Bundle today and get ready for your Highland vacation.
Top Hotel Deals
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the overall value in our reviews. ...
Motel 6 - Chicago, IL
10022 South Halsted Street Chicago IL
Stay at this motel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Abbott Park and Martin Luther King Drive are located ...
DoubleTree by Hilton Chicago - Alsip
5000 W 127th St Alsip IL
Book a stay at this business-friendly hotel in Alsip. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Wind Creek Southland Casino and Hotel
17300 S Halsted St Hazel Crest IL
Book a stay at this spa resort in Hazel Crest. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Ravisloe Country Club and Oak Hill ...
Quality Inn & Suites Orland Park - Chicago
8800 W 159th St Orland Park IL
Book a stay at this business-friendly hotel in Orland Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Baymont by Wyndham Chicago/Alsip
12801 South Cicero Alsip IL
Book a stay at this business-friendly hotel in Alsip. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Ameristar Casino Hotel East Chicago
777 Ameristar Blvd. East Chicago IN
Book a stay at this beach hotel in East Chicago. Enjoy free parking, 5 restaurants, and a marina. Our guests praise the helpful staff and the clean rooms in ...
EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
18501 Convention Center Drive Tinley Park IL
Book a stay at this business-friendly hotel in Tinley Park. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the breakfast and the helpful ...
Days Inn and Suites by Wyndham Hammond, IN
4000 Calumet Avenue Hammond IN
Book a stay at this business-friendly hotel in Hammond. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff in our ...
Super 8 by Wyndham South Holland
17225 Halsted St South Holland IL
Book a stay at this business-friendly hotel in South Holland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Hyatt Place Chicago-South/University Medical Center
5225 S Harper Ave Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free area shuttle. Our guests praise the helpful staff in our ...
Sophy Hyde Park
1411 East 53rd Street Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular ...
Motel 6 Hammond, IN - Chicago Area
3840 179th St Hammond IN
Stay at this motel in Hammond. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the clean rooms in our reviews. Popular attractions ...
Luxe Inn and Suites
1335 E. SIBLEY BLVD. Dolton IL
Stay at this motel in Dolton. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Veterans Memorial Park and River Oaks Center are located ...
Super 8 by Wyndham Merrillville
8300 Louisiana St Merrillville IN
Book a stay at this business-friendly hotel in Merrillville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
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 14 - Wed, Oct 21
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$148
Roundtrip
found 21 hours ago
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$193
Roundtrip
found 21 hours ago
Tue, Sep 29 - Sat, Oct 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$195
Roundtrip
found 6 days ago
Tue, Sep 29 - Sat, Oct 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$195
Roundtrip
found 6 days ago
Fri, Oct 2 - Mon, Oct 5
LAX
Los Angeles Intl.
MDW
Midway Intl.
$207
Roundtrip
found 6 hours ago
Best neighborhoods in Highland
Best points of interest in Highland
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