Search Deals onHighland Vacation Packages
Highland Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Price was $487, price is now $319 per person
$319
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
The Talbott, Autograph Collection
Price was $652, price is now $396 per person
$396
per person
Dec 10 - Dec 13
found 1 day 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.
Hotel Riu Plaza Chicago
Price was $728, price is now $453 per person
$453
per person
Dec 10 - Dec 13
found 1 day 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.
Sheraton Grand Chicago Riverwalk
Price was $599, price is now $377 per person
$377
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pendry Chicago
Price was $824, price is now $520 per person
$520
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Beautiful rooms and service.
Reviewed on Nov 5, 2026
Eurostars Magnificent Mile
Price was $625, price is now $403 per person
$403
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The room itself was pretty clean, it had a good shower which is sometimes rare to find. The staff was friendly and housekeeping was responsive. Close to things, but I wouldn’t necessarily say walking distance. It was pretty noisy but hard to get away from that in a city.
Reviewed on Nov 7, 2026
Level Chicago Fulton Market
Price was $857, price is now $557 per person
$557
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Weird space w the way the bed is no access off the side and the counter was stained badly. There was a 28$ additional amenity fee that they slapped on upon check in. The pool is closed and didn’t use the weight room it was a one night stay. over priced but could be ok for a long stay w the kitchen
Reviewed on Nov 6, 2026
Level Chicago - River North
Price was $630, price is now $419 per person
$419
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Highland Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Highland Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Fri, Dec 4 - Wed, Dec 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 6 hours ago
$189
Roundtrip
found 6 hours ago
Tue, Jan 5 - Tue, Jan 19
LAX
Los Angeles Intl.
MDW
Midway Intl.
$247 Roundtrip, found 1 hour ago
$247
Roundtrip
found 1 hour ago
Mon, Nov 9 - Mon, Feb 1
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,140 Roundtrip, just found
$1,140
Roundtrip
just found
Sun, Nov 8 - Mon, Feb 1
SHA
Hongqiao Intl.
ORD
O'Hare Intl.
$4,382 Roundtrip, found 1 hour ago
$4,382
Roundtrip
found 1 hour ago
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