Search Deals onHighland Park Vacation Packages
Highland Park Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Save 100% on your flight
Price was $520, price is now $356 per person
$356
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Great experience the staff was super friendly and the hotel location was just amazing right in downtown Chicago. I will definitely be staying there again..
Reviewed on Jul 18, 2026
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,541, price is now $874 per person
$874
per person
Sep 23 - Sep 28
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 $1,237, price is now $751 per person
$751
per person
Sep 25 - Sep 29
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.
Level hotels are awesome
Reviewed on Jul 18, 2026
LondonHouse Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $1,269, price is now $829 per person
$829
per person
Sep 25 - Sep 29
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 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.
Great location, we walked everywhere, but the bus stopped in front of the hotel. The River Walk is right across the street. The rooftop bar has an amazing view of the city.
Reviewed on Jul 18, 2026
Hotel Felix River North/Magnificent Mile
Save 100% on your flight
Price was $680, price is now $460 per person
$460
per person
Sep 27 - Oct 1
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.
Nice staff, easy check-in, and about an 8 minute walk to red line which can get you all over town. No complaints about our stay.
Reviewed on Jul 18, 2026
Hotel Saint Clair- Magnificent Mile
Save 100% on your flight
Price was $546, price is now $372 per person
$372
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Clean room but the bathroom is the smallest one I've experienced in a hotel.
Reviewed on Jul 18, 2026
Hilton Chicago O'Hare Airport
Save 100% on your flight
Price was $1,047, price is now $714 per person
$714
per person
Sep 23 - Sep 28
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 Fashion Outlets of Chicago and Rosemont Theatre are located nearby.
Hilton Garden Inn Chicago Downtown South Loop
Save 100% on your flight
Price was $990, price is now $677 per person
$677
per person
Sep 25 - Sep 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 WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
Must staff were pleasant.
Reviewed on Jul 18, 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.
Tue, Aug 11 - Thu, Aug 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$183 Roundtrip, found 6 days ago
$183
Roundtrip
found 6 days ago
Fri, Oct 23 - Mon, Oct 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 9 hours ago
$237
Roundtrip
found 9 hours ago
Thu, Aug 27 - Sat, Aug 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$252 Roundtrip, found 12 hours ago
$252
Roundtrip
found 12 hours ago
Tue, Sep 1 - Fri, Sep 18
PEK
Capital Intl.
ORD
O'Hare Intl.
$1,190 Roundtrip, found 11 hours ago
$1,190
Roundtrip
found 11 hours ago
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