Search Deals onHillsdale Vacation Packages
Hillsdale Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection
Price was $601, price is now $445 per person
$445
per person
Oct 23 - Oct 25
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.
This hotel is situated in a prime location, making it convenient to get anywhere in Chicago. The staff always greeted guests with bright smiles and provided immediate, friendly assistance with even the smallest requests. The room was very spacious; while there was some noise from neighboring rooms, it wasn't bothersome enough to be a major issue. I would love to stay here again if I visit Chicago in the future.
Reviewed on Jul 24, 2026
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $843, price is now $506 per person
$506
per person
Sep 6 - Sep 9
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,nice location,I'm would come again..
Reviewed on Jul 27, 2026
Four Seasons Hotel Chicago
Save 100% on your flight
Price was $2,737, price is now $1,765 per person
$1,765
per person
Oct 13 - Oct 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 breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Felix River North/Magnificent Mile
Save 100% on your flight
Price was $761, price is now $501 per person
$501
per person
Sep 5 - Sep 8
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.
The Langham, Chicago
Save 100% on your flight
Price was $3,196, price is now $2,230 per person
$2,230
per person
Oct 13 - Oct 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 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 Peninsula Chicago
Save 100% on your flight
Price was $3,266, price is now $2,291 per person
$2,291
per person
Oct 13 - Oct 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 property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pendry Chicago
Save 100% on your flight
Price was $2,464, price is now $1,804 per person
$1,804
per person
Oct 13 - Oct 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 rooftop terrace, 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.
Best location and a beautiful hotel
Reviewed on Jul 26, 2026
Level Chicago – Old Town
Price was $610, price is now $452 per person
$452
per person
Oct 23 - Oct 25
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.
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.
Tue, Dec 15 - Tue, Jan 5
AUS
Austin-Bergstrom Intl.
MLI
Quad City Intl.
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Wed, Jul 29 - Sat, Aug 1
LAS
Harry Reid Intl.
MLI
Quad City Intl.
$290 Roundtrip, found 1 day ago
$290
Roundtrip
found 1 day ago
Wed, Jul 29 - Wed, Aug 5
ATL
Hartsfield-Jackson Atlanta Intl.
MLI
Quad City Intl.
$293 Roundtrip, found 1 day ago
$293
Roundtrip
found 1 day ago
Fri, Sep 11 - Mon, Sep 21
DEN
Denver Intl.
MLI
Quad City Intl.
$293 Roundtrip, found 1 day ago
$293
Roundtrip
found 1 day ago
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