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Hillside Vacation Packages

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Hillside Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
Price was $803, price is now $587 per person
$587
per person
Jun 5 - Jun 7
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 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,469, price is now $924 per person
$924
per person
May 29 - Jun 1
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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $971, price is now $612 per person
$612
per person
Jun 5 - Jun 7
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 – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,393, price is now $885 per person
$885
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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.
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 $1,698, price is now $1,094 per person
$1,094
per person
May 29 - Jun 1
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.
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $2,488, price is now $1,654 per person
$1,654
per person
May 29 - Jun 1
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 bars/lounges, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. 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 $1,205, price is now $837 per person
$837
per person
May 29 - Jun 1
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.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Price was $1,618, price is now $1,186 per person
$1,186
per person
May 15 - May 18
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.

Hillside Vacation Packages 3-4 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 $1,294, price is now $711 per person
$711
per person
Jun 4 - Jun 7
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 $1,161, price is now $721 per person
$721
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,469, price is now $924 per person
$924
per person
May 29 - Jun 1
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 $1,393, price is now $885 per person
$885
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)

Hillside Vacation Packages 5-7 Night Stays

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

The Wade

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,528, price is now $894 per person
$894
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,983, price is now $1,020 per person
$1,020
per person
Jun 4 - Jun 9
found 13 hours 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 $1,975, price is now $1,162 per person
$1,162
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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 $1,744, price is now $1,032 per person
$1,032
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)

Top Flight Deals

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

Frontier Airlines
Tue, Apr 28 - Wed, May 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$108 Roundtrip, found 1 hour ago
$108
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Apr 28 from Los Angeles Intl. to O'Hare Intl., returning Wed, May 13, priced at $108 found 1 hour ago
Frontier Airlines
Thu, Apr 9 - Tue, Apr 14
LAX
Los Angeles Intl.
MDW
Midway Intl.
$212 Roundtrip, found 1 hour ago
$212
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Apr 9 from Los Angeles Intl. to Midway Intl., returning Tue, Apr 14, priced at $212 found 1 hour ago
American Airlines
Sat, Jul 18 - Sat, Jul 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$532 Roundtrip, found 1 hour ago
$532
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sat, Jul 18 from Los Angeles Intl. to Greater Rockford, returning Sat, Jul 25, priced at $532 found 1 hour ago
Asiana Airlines
Wed, Jun 3 - Mon, Sep 7
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,155 Roundtrip, found 9 hours ago
$1,155
Roundtrip
found 9 hours ago
Select Asiana Airlines flight, departing Wed, Jun 3 from Pudong Intl. to O'Hare Intl., returning Mon, Sep 7, priced at $1,155 found 9 hours ago