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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 Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $564, price is now $335 per person
$335
per person
Nov 14 - Nov 16
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.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,310, price is now $738 per person
$738
per person
Oct 31 - Nov 5
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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
Price was $1,031, price is now $589 per person
$589
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, 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.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Save 100% on your flight
Price was $943, price is now $546 per person
$546
per person
Dec 13 - Dec 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $1,091, price is now $648 per person
$648
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
Price was $1,037, price is now $633 per person
$633
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Save 100% on your flight
Price was $893, price is now $555 per person
$555
per person
Dec 13 - Dec 20
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 24-hour fitness center, and valet parking (surcharge). Our guests praise the pool and the restaurant 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 $1,002, price is now $638 per person
$638
per person
Oct 31 - Nov 5
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, 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.

Highland Park Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove

DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove

4 out of 5
Price was $344, price is now $229 per person
$229
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,105, price is now $648 per person
$648
per person
Dec 11 - Dec 14
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 $520, price is now $327 per person
$327
per person
Nov 10 - Nov 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $677, price is now $453 per person
$453
per person
Nov 10 - Nov 13
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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,094, price is now $561 per person
$561
per person
Dec 2 - Dec 8
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $2,332, price is now $1,304 per person
$1,304
per person
Dec 2 - Dec 8
found 14 hours 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 $1,310, price is now $738 per person
$738
per person
Oct 31 - Nov 5
found 1 day 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 $1,031, price is now $589 per person
$589
per person
Oct 31 - Nov 5
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
Sat, Nov 1 - Mon, Nov 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$152 Roundtrip, found 8 hours ago
$152
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sat, Nov 1 from Los Angeles Intl. to O'Hare Intl., returning Mon, Nov 3, priced at $152 found 8 hours ago
Spirit Airlines
Wed, Nov 12 - Wed, Nov 12
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$154 Roundtrip, found 11 hours ago
$154
Roundtrip
found 11 hours ago
Select Spirit Airlines flight, departing Wed, Nov 12 from Los Angeles Intl. to O'Hare Intl., returning Wed, Nov 12, priced at $154 found 11 hours ago
Frontier Airlines
Thu, Oct 30 - Thu, Nov 6
LAX
Los Angeles Intl.
MDW
Midway Intl.
$179 Roundtrip, found 18 hours ago
$179
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Thu, Oct 30 from Los Angeles Intl. to Midway Intl., returning Thu, Nov 6, priced at $179 found 18 hours ago
Air China
Tue, Nov 4 - Sun, Nov 23
PVG
Pudong Intl.
ORD
O'Hare Intl.
$961 Roundtrip, found 3 days ago
$961
Roundtrip
found 3 days ago
Select Air China flight, departing Tue, Nov 4 from Pudong Intl. to O'Hare Intl., returning Sun, Nov 23, priced at $961 found 3 days ago