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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.
The Glen Club

The Glen Club

4 out of 5
Save 100% on your flight
Price was $450, price is now $295 per person
$295
per person
Dec 5 - Dec 8
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this golf hotel in Glenview. Enjoy free WiFi, free parking, and a golf course. Our guests praise the helpful staff in our reviews. Popular attractions The Glen Club and The Glen Town Center are located nearby.

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $837, price is now $500 per person
$500
per person
Dec 8 - Dec 13
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. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
El edificio es muy bueno, la atención del personal pésimo, siempre mal predispuestos para ayudar!

Reviewed on Oct 17, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $928, price is now $560 per person
$560
per person
Dec 18 - Dec 23
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.
Clean room, great staff

Reviewed on Oct 17, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $2,006, price is now $1,282 per person
$1,282
per person
Nov 22 - Nov 27
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 and the clean rooms in our reviews. Popular attractions Chicago Riverwalk 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 $875, price is now $594 per person
$594
per person
Dec 17 - Dec 20
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.
The stay was all good as represented on the site!

Reviewed on Oct 12, 2026

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Save 100% on your flight
Price was $660, price is now $451 per person
$451
per person
Dec 8 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk 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 $648, price is now $447 per person
$447
per person
Dec 18 - Dec 21
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.

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was $503, price is now $353 per person
$353
per person
Dec 24 - Dec 26
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.
Excellent staff, excellent location, great resort style breakfast buffet

Reviewed on Oct 17, 2026

Highland Park Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Glen Club

The Glen Club

4 out of 5
Save 100% on your flight
Price was $450, price is now $295 per person
$295
per person
Dec 5 - Dec 8
found 24 hours 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 $1,454, price is now $882 per person
$882
per person
Dec 24 - Dec 27
found 20 hours 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 $578, price is now $354 per person
$354
per person
Dec 18 - Dec 21
found 1 day 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 $703, price is now $472 per person
$472
per person
Dec 5 - Dec 8
found 21 hours 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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $853, price is now $471 per person
$471
per person
Dec 8 - Dec 13
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 $876, price is now $514 per person
$514
per person
Dec 18 - Dec 23
found 1 day 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 $1,144, price is now $684 per person
$684
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $928, price is now $560 per person
$560
per person
Dec 18 - Dec 23
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
Wed, Dec 30 - Mon, Jan 4
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$187 Roundtrip, just found
$187
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Dec 30 from Los Angeles Intl. to O'Hare Intl., returning Mon, Jan 4, priced at $187 just found
Delta
Mon, Nov 16 - Tue, Nov 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$227 Roundtrip, found 2 days ago
$227
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Nov 16 from Los Angeles Intl. to O'Hare Intl., returning Tue, Nov 17, priced at $227 found 2 days ago
Frontier Airlines
Thu, Nov 19 - Sat, Dec 5
LAX
Los Angeles Intl.
MDW
Midway Intl.
$264 Roundtrip, found 5 days ago
$264
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Nov 19 from Los Angeles Intl. to Midway Intl., returning Sat, Dec 5, priced at $264 found 5 days ago
Philippine Airlines
Fri, Nov 13 - Wed, Dec 2
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,102 Roundtrip, just found
$1,102
Roundtrip
just found
Select Philippine Airlines flight, departing Fri, Nov 13 from Pudong Intl. to O'Hare Intl., returning Wed, Dec 2, priced at $1,102 just found