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Highland Vacation Packages

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Highland Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $801, price is now $517 per person
$517
per person
Oct 22 - Oct 25
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 helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,273, price is now $734 per person
$734
per person
Oct 21 - Oct 25
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.

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,866, price is now $1,106 per person
$1,106
per person
Sep 19 - Sep 24
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.
Great property. Prime location. Enjoyed my stay and would stay there again.

Reviewed on Aug 12, 2026

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 $2,792, price is now $1,664 per person
$1,664
per person
Sep 13 - Sep 19
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.

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Save 100% on your flight
Price was $4,897, price is now $2,949 per person
$2,949
per person
Sep 13 - Sep 19
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 in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The

Reviewed on Aug 10, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $2,834, price is now $1,719 per person
$1,719
per person
Sep 13 - Sep 19
found 2 days 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.

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
Price was $2,304, price is now $1,469 per person
$1,469
per person
Sep 13 - Sep 19
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.

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $2,168, price is now $1,411 per person
$1,411
per person
Sep 13 - Sep 19
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.
nice property

Reviewed on Aug 12, 2026

Highland Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $801, price is now $517 per person
$517
per person
Oct 22 - Oct 25
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 $1,273, price is now $734 per person
$734
per person
Oct 21 - Oct 25
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 $1,368, price is now $888 per person
$888
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,988, price is now $1,306 per person
$1,306
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Highland Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,230, price is now $661 per person
$661
per person
Oct 28 - Nov 3
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was $1,613, price is now $796 per person
$796
per person
Oct 28 - Nov 3
found 23 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 $1,524, price is now $755 per person
$755
per person
Oct 28 - Nov 3
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,249, price is now $692 per person
$692
per person
Oct 28 - Nov 3
found 20 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
Wed, Oct 28 - Tue, Nov 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$162 Roundtrip, just found
$162
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Oct 28 from Los Angeles Intl. to O'Hare Intl., returning Tue, Nov 3, priced at $162 just found
Frontier Airlines
Sat, Sep 26 - Sat, Oct 3
LAX
Los Angeles Intl.
MDW
Midway Intl.
$179 Roundtrip, just found
$179
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Sep 26 from Los Angeles Intl. to Midway Intl., returning Sat, Oct 3, priced at $179 just found
American Airlines
Wed, Sep 2 - Tue, Sep 8
LAX
Los Angeles Intl.
RFD
Greater Rockford
$264 Roundtrip, found 1 day ago
$264
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Sep 2 from Los Angeles Intl. to Greater Rockford, returning Tue, Sep 8, priced at $264 found 1 day ago
Air China
Tue, Sep 1 - Fri, Sep 18
PEK
Capital Intl.
ORD
O'Hare Intl.
$1,291 Roundtrip, found 2 hours ago
$1,291
Roundtrip
found 2 hours ago
Select Air China flight, departing Tue, Sep 1 from Capital Intl. to O'Hare Intl., returning Fri, Sep 18, priced at $1,291 found 2 hours ago