Search Deals onHighland Park Vacation Packages
Highland Park Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Save 100% on your flight
Price was $479, price is now $330 per person
$330
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Ok
Reviewed on Oct 6, 2026
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $1,276, price is now $829 per person
$829
per person
Nov 12 - Nov 15
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 full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The Talbott, Autograph Collection
Save 100% on your flight
Price was $764, price is now $504 per person
$504
per person
Nov 19 - Nov 22
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
Save 100% on your flight
Price was $931, price is now $614 per person
$614
per person
Nov 19 - Nov 22
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.
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination
Save 100% on your flight
Price was $1,049, price is now $694 per person
$694
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Joliet. Enjoy free WiFi, 3 restaurants, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Route 66 Raceway and Harrah's Casino are located nearby.
Pendry Chicago
Save 100% on your flight
Price was $773, price is now $513 per person
$513
per person
Dec 17 - Dec 20
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.
Fantastic stay!
Reviewed on Oct 6, 2026
Level Chicago – Old Town
Save 100% on your flight
Price was $724, price is now $482 per person
$482
per person
Dec 3 - Dec 6
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) 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, great amenities.
Reviewed on Oct 6, 2026
The Emily Hotel
Save 100% on your flight
Price was $580, price is now $404 per person
$404
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly 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 United Center and Chicago Riverwalk are located nearby.
Unique stay and fun location. Staff was thoughtful.
Reviewed on Oct 8, 2026
Highland Park Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Highland Park 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.
Wed, Nov 18 - Thu, Nov 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$138 Roundtrip, found 4 hours ago
$138
Roundtrip
found 4 hours ago
Wed, Nov 18 - Thu, Nov 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$145 Roundtrip, found 4 hours ago
$145
Roundtrip
found 4 hours ago
Thu, Nov 26 - Wed, Dec 9
LAX
Los Angeles Intl.
MDW
Midway Intl.
$187 Roundtrip, found 2 hours ago
$187
Roundtrip
found 2 hours ago
Fri, Nov 13 - Mon, Nov 30
PVG
Pudong Intl.
ORD
O'Hare Intl.
$927 Roundtrip, found 2 hours ago
$927
Roundtrip
found 2 hours ago
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