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 $842, price is now $557 per person
$557
per person
Sep 3 - Sep 6
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.
Rooms were very old. There was blk mold or something in the shower. Window was broken too.
Reviewed on Jul 1, 2026
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,320, price is now $829 per person
$829
per person
Sep 15 - Sep 18
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.
Highly recommend
Reviewed on Jul 1, 2026
Level Chicago – Old Town
Save 100% on your flight
Price was $1,376, price is now $926 per person
$926
per person
Aug 6 - Aug 9
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.
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026
The Emily Hotel
Save 100% on your flight
Price was $1,074, price is now $725 per person
$725
per person
Sep 15 - Sep 18
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.
Very unique motif
Reviewed on Jul 1, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $1,261, price is now $880 per person
$880
per person
Sep 3 - Sep 6
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, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Great stay; fabulous location, amazing views and access to so much; friendly staff. Super friendly and accommodating housekeeping! Food/bar service took a long long time, every time..long wait to order…long wait to get drinks…long wait to pay bill. Not enough staff behind the bar.
Reviewed on Jun 30, 2026
Level Chicago - River North
Save 100% on your flight
Price was $863, price is now $607 per person
$607
per person
Sep 18 - Sep 20
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.
Not for family it will work for chilling with your ex or old friends
Reviewed on Jun 29, 2026
Omni Chicago Hotel
Save 100% on your flight
Price was $818, price is now $575 per person
$575
per person
Aug 21 - Aug 24
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 breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Very clean, great location. Every staff member we encountered was just terrific
Reviewed on Jun 30, 2026
Eurostars Magnificent Mile
Save 100% on your flight
Price was $1,115, price is now $796 per person
$796
per person
Sep 15 - Sep 18
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.
Always came back to a very well clean room, thank you Rosa!
Reviewed on Jun 30, 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.
Mon, Aug 31 - Tue, Sep 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$180 Roundtrip, found 1 day ago
$180
Roundtrip
found 1 day ago
Sun, Aug 9 - Mon, Aug 24
LAX
Los Angeles Intl.
MDW
Midway Intl.
$252 Roundtrip, found 1 day ago
$252
Roundtrip
found 1 day ago
Sat, Jul 18 - Sat, Jul 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$419 Roundtrip, found 6 days ago
$419
Roundtrip
found 6 days ago
Wed, Jul 8 - Wed, Jul 22
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$742 Roundtrip, found 4 hours ago
$742
Roundtrip
found 4 hours ago
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