Search Deals onHillsdale Vacation Packages
Hillsdale Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Save 100% on your flight
Price was $985, price is now $620 per person
$620
per person
Oct 16 - Oct 19
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.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,341, price is now $734 per person
$734
per person
Oct 16 - Oct 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 breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Very clean, high end hotel.
Reviewed on Jul 23, 2026
Level Chicago Fulton Market
Save 100% on your flight
Price was $2,043, price is now $1,151 per person
$1,151
per person
Oct 11 - Oct 17
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.
Hotel Felix River North/Magnificent Mile
Save 100% on your flight
Price was $1,477, price is now $862 per person
$862
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
We really enjoyed our stay. clean rooms and staff was very friendly
Reviewed on Jul 22, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $2,214, price is now $1,331 per person
$1,331
per person
Oct 11 - Oct 17
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 was nice and close to the amenities of the pier. Only downside was most attractions are in the city which makes this location not as ideal.
Reviewed on Jul 22, 2026
The Talbott, Autograph Collection
Save 100% on your flight
Price was $1,614, price is now $1,046 per person
$1,046
per person
Oct 11 - Oct 17
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.
LondonHouse Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $1,417, price is now $953 per person
$953
per person
Sep 25 - Sep 29
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.
Location was great for us, very short walking distance to board architecture cruise and also for the hop on hop off bus tours.
The hotel rooftop is a real plus, if you can get a table or a seat at the bar, the traffic is very heavy.
Our suite was excellent with beautiful views of the waterways.
Reviewed on Jul 23, 2026
Eurostars Magnificent Mile
Save 100% on your flight
Price was $1,747, price is now $1,192 per person
$1,192
per person
Oct 11 - Oct 17
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.
Everything was great!
Reviewed on Jul 22, 2026
Hillsdale Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Hillsdale Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sun, Sep 6 - Wed, Sep 23
AUS
Austin-Bergstrom Intl.
MLI
Quad City Intl.
$231 Roundtrip, found 5 days ago
$231
Roundtrip
found 5 days ago
Mon, Sep 14 - Mon, Sep 21
DEN
Denver Intl.
MLI
Quad City Intl.
$286 Roundtrip, found 3 days ago
$286
Roundtrip
found 3 days ago
Tue, Jul 28 - Tue, Aug 4
LAS
Harry Reid Intl.
MLI
Quad City Intl.
$355 Roundtrip, found 4 days ago
$355
Roundtrip
found 4 days ago
Wed, Jul 29 - Wed, Aug 5
ATL
Hartsfield-Jackson Atlanta Intl.
MLI
Quad City Intl.
$489 Roundtrip, found 20 hours ago
$489
Roundtrip
found 20 hours ago
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