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Highland Park Vacation Packages

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Highland Park Flight + Hotel Packages

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
Save 100% on your flight
Price was $754, price is now $491 per person
$491
per person
Jul 24 - Jul 27
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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,629, price is now $906 per person
$906
per person
Jul 30 - Aug 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 breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,553, price is now $918 per person
$918
per person
Jul 22 - Jul 27
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 parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,718, price is now $1,045 per person
$1,045
per person
Jul 30 - Aug 2
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.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $931, price is now $589 per person
$589
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $1,563, price is now $994 per person
$994
per person
Jul 30 - Aug 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, 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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,247, price is now $810 per person
$810
per person
Jul 2 - Jul 5
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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,049, price is now $711 per person
$711
per person
Jul 9 - Jul 12
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.

Highland Park Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $931, price is now $589 per person
$589
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,629, price is now $906 per person
$906
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,718, price is now $1,045 per person
$1,045
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,563, price is now $994 per person
$994
per person
Jul 30 - Aug 2
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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,411, price is now $768 per person
$768
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,540, price is now $834 per person
$834
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,553, price is now $918 per person
$918
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,620, price is now $999 per person
$999
per person
Jul 22 - Jul 27
found 1 day 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
Sun, May 24 - Wed, Jun 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$158 Roundtrip, found 4 days ago
$158
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, May 24 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jun 3, priced at $158 found 4 days ago
Delta
Wed, Jul 22 - Wed, Jul 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$219 Roundtrip, found 3 days ago
$219
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Jul 22 from Los Angeles Intl. to Midway Intl., returning Wed, Jul 29, priced at $219 found 3 days ago
American Airlines
Sun, May 24 - Sun, May 31
LAX
Los Angeles Intl.
RFD
Greater Rockford
$404 Roundtrip, found 5 days ago
$404
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sun, May 24 from Los Angeles Intl. to Greater Rockford, returning Sun, May 31, priced at $404 found 5 days ago
Icelandair
Thu, Jul 9 - Sat, Jul 18
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$883 Roundtrip, found 13 hours ago
$883
Roundtrip
found 13 hours ago
Select Icelandair flight, departing Thu, Jul 9 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Sat, Jul 18, priced at $883 found 13 hours ago