Search Deals onHighland Park Vacation Packages
Highland Park Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Chicago Magnificent Mile
Save 100% on your flight
Price was $339, price is now $238 per person
$238
per person
Feb 27 - Mar 2
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 Michigan Avenue and Chicago Riverwalk are located nearby.
La Banque Hotel
Save 100% on your flight
Price was $667, price is now $403 per person
$403
per person
Apr 3 - Apr 6
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $438, price is now $281 per person
$281
per person
Mar 27 - Mar 29
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.
Level Chicago – Old Town
Save 100% on your flight
Price was $1,125, price is now $726 per person
$726
per person
Mar 17 - Mar 24
found 1 day 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.
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $1,221, price is now $807 per person
$807
per person
Mar 6 - Mar 10
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 French Country Inn Lake Geneva
Save 100% on your flight
Price was $456, price is now $315 per person
$315
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this hotel in Lake Geneva. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Geneva National Golf Club and Lake Como are located nearby.
Hilton Chicago O'Hare Airport
Save 100% on your flight
Price was $389, price is now $271 per person
$271
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
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 staff and the clean rooms in our reviews. Popular attractions Allstate Arena and The Dome at the Parkway Bank Sports Complex are located nearby.
Holiday Inn Club Vacations at Lake Geneva Resort by IHG
Save 100% on your flight
Price was $407, price is now $286 per person
$286
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this spa resort in Lake Geneva. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions The Highlands Golf Course and The Brute Golf Course are located nearby.
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.
Tue, Mar 24 - Mon, Apr 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$142 Roundtrip, found 3 hours ago
$142
Roundtrip
found 3 hours ago
Wed, Feb 11 - Mon, Feb 23
LAX
Los Angeles Intl.
MDW
Midway Intl.
$211 Roundtrip, found 4 days ago
$211
Roundtrip
found 4 days ago
Tue, Mar 17 - Wed, Mar 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$243 Roundtrip, found 1 day ago
$243
Roundtrip
found 1 day ago
Thu, Jan 29 - Tue, Feb 3
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$572 Roundtrip, found 3 days ago
$572
Roundtrip
found 3 days ago
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