Search Deals on
Highland Park Vacation Packages

Build your package with 2 more options
Photo by Meghan hernandez

Highland Park Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $247, price is now $151 per person
$151
per person
Nov 25 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star 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.
The Blackstone, Autograph Collection

The Blackstone, Autograph Collection

4 out of 5
Save 100% on your flight
Price was $457, price is now $238 per person
$238
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy a 24-hour fitness center, parking (surcharge), and onsite spa services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
The Emily Hotel

The Emily Hotel

4 out of 5
Price was $521, price is now $280 per person
$280
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $296, price is now $169 per person
$169
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $293, price is now $171 per person
$171
per person
Nov 25 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $597, price is now $358 per person
$358
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Save 100% on your flight
Price was $454, price is now $272 per person
$272
per person
Dec 30 - Jan 3
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 a fitness center. Popular attractions United Center and Chicago Riverwalk are located nearby.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Save 100% on your flight
Price was $1,346, price is now $816 per person
$816
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Highland Park Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $296, price is now $169 per person
$169
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Blackstone, Autograph Collection

The Blackstone, Autograph Collection

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $457, price is now $238 per person
$238
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $521, price is now $280 per person
$280
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $597, price is now $358 per person
$358
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Highland Park Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $707, price is now $360 per person
$360
per person
Dec 10 - Dec 15
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,721, price is now $766 per person
$766
per person
Nov 25 - Dec 2
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $928, price is now $478 per person
$478
per person
Nov 25 - Dec 2
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $1,225, price is now $651 per person
$651
per person
Nov 25 - Dec 2
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Sat, Nov 15 - Sun, Nov 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$84 Roundtrip, found 1 day ago
$84
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Nov 15 from Los Angeles Intl. to O'Hare Intl., returning Sun, Nov 16, priced at $84 found 1 day ago
American Airlines
Fri, Jan 9 - Sun, Jan 11
LAX
Los Angeles Intl.
RFD
Greater Rockford
$189 Roundtrip, found 9 hours ago
$189
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Fri, Jan 9 from Los Angeles Intl. to Greater Rockford, returning Sun, Jan 11, priced at $189 found 9 hours ago
Delta
Tue, Jan 6 - Mon, Jan 12
LAX
Los Angeles Intl.
MDW
Midway Intl.
$217 Roundtrip, found 3 hours ago
$217
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Jan 6 from Los Angeles Intl. to Midway Intl., returning Mon, Jan 12, priced at $217 found 3 hours ago
All Nippon Airways
Wed, Nov 5 - Mon, Dec 1
PVG
Pudong Intl.
ORD
O'Hare Intl.
$997 Roundtrip, found 2 days ago
$997
Roundtrip
found 2 days ago
Select All Nippon Airways flight, departing Wed, Nov 5 from Pudong Intl. to O'Hare Intl., returning Mon, Dec 1, priced at $997 found 2 days ago