Search Deals on
Hillsdale Vacation Packages

Build your package with 2 more options

Hillsdale Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Comfort Suites Elgin Northwest

Comfort Suites Elgin Northwest

2.5 out of 5
Save 100% on your flight
Price was $388, price is now $267 per person
$267
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Elgin. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Randall Oaks Golf Club and Cinemark West Dundee are located nearby.
Un

Reviewed on Sep 28, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,059, price is now $604 per person
$604
per person
Oct 29 - Nov 2
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.
👍

Reviewed on Sep 28, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $986, price is now $602 per person
$602
per person
Nov 20 - Nov 22
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.
The Trump hotel is right in the middle of downtown, but it's on the quieter side of the river from the other hotels. It offers direct access to the river where you can join the architecture river tour and is overall quieter than the hotels on the other side of the river. The self parking is a bit of a tricky drive up very narrow and curving ramps. If you drive a Suburban or a Cybertruck, you might have difficulty.

Reviewed on Sep 29, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,211, price is now $741 per person
$741
per person
Oct 29 - Nov 2
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 location is perfect and the building is quite nice. The rooms are also comfortable. This is not a hotel, but rather occupies several floors in a large apartment building. We had a couple issues with our room (malfunctioning, smoke alarm and empty body wash) and neither were dealt with despite a asking multiple times.

Reviewed on Sep 27, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Save 100% on your flight
Price was $1,816, price is now $1,165 per person
$1,165
per person
Nov 22 - Nov 26
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 property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
It is the greatest will be there again

Reviewed on Sep 29, 2026

Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel

4 out of 5
Save 100% on your flight
Price was $1,051, price is now $694 per person
$694
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
It was very clean & great staff. Awesome river front view. Best hotel in Chicago Downtown

Reviewed on Sep 28, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
Price was $1,102, price is now $749 per person
$749
per person
Nov 4 - Nov 8
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.

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $943, price is now $650 per person
$650
per person
Nov 20 - Nov 23
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.

Hillsdale 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 $862, price is now $547 per person
$547
per person
Nov 20 - Nov 23
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 $1,059, price is now $604 per person
$604
per person
Oct 29 - Nov 2
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 $1,211, price is now $741 per person
$741
per person
Oct 29 - Nov 2
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 $1,267, price is now $783 per person
$783
per person
Nov 20 - Nov 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.

Bargain Flight
Tue, Dec 1 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
MLI
Quad City Intl.
$232 Roundtrip, found 4 hours ago
$232
Roundtrip
found 4 hours ago
Select Bargain Flight flight, departing Tue, Dec 1 from Hartsfield-Jackson Atlanta Intl. to Quad City Intl., returning Tue, Dec 8, priced at $232 found 4 hours ago
Bargain Flight
Sat, Jan 9 - Sat, Jan 23
AUS
Austin-Bergstrom Intl.
MLI
Quad City Intl.
$244 Roundtrip, found 1 day ago
$244
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sat, Jan 9 from Austin-Bergstrom Intl. to Quad City Intl., returning Sat, Jan 23, priced at $244 found 1 day ago
United
Tue, Oct 13 - Tue, Oct 20
DEN
Denver Intl.
MLI
Quad City Intl.
$339 Roundtrip, found 4 days ago
$339
Roundtrip
found 4 days ago
Select United flight, departing Tue, Oct 13 from Denver Intl. to Quad City Intl., returning Tue, Oct 20, priced at $339 found 4 days ago
United
Wed, Nov 18 - Wed, Nov 25
SAN
San Diego Intl.
MLI
Quad City Intl.
$348 Roundtrip, found 12 hours ago
$348
Roundtrip
found 12 hours ago
Select United flight, departing Wed, Nov 18 from San Diego Intl. to Quad City Intl., returning Wed, Nov 25, priced at $348 found 12 hours ago