Hampshire Vacations

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

Top Hotel Deals

Super 8 by Wyndham Hampshire IL

Super 8 by Wyndham Hampshire IL

2 out of 5
115 Arrowhead Drive Hampshire IL
5.81 km from city center
Book a stay at this business-friendly motel in Hampshire. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Goebbert's Farm and Donley's ...
Hyatt Place Chicago/Hoffman Estates

Hyatt Place Chicago/Hoffman Estates

3 out of 5
2750 Greenspoint Pkwy Hoffman Estates IL
31.92 km from city center
Book a stay at this business-friendly hotel in Hoffman Estates. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Comfort Inn & Suites Geneva - West Chicago

Comfort Inn & Suites Geneva - West Chicago

2.5 out of 5
1555 E Fabyan Pkwy Geneva IL
32.97 km from city center
Book a stay at this business-friendly hotel in Geneva. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Hampton Inn & Suites Chicago/Hoffman Estates

Hampton Inn & Suites Chicago/Hoffman Estates

2.5 out of 5
2825 Greenspoint Pkwy Hoffman Estates IL
31.59 km from city center
Stay at this hotel in Hoffman Estates. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
AmericInn by Wyndham Woodstock IL

AmericInn by Wyndham Woodstock IL

2.5 out of 5
990 Lake Avenue Woodstock IL
24.25 km from city center
Book a stay at this ski hotel in Woodstock. Enjoy free breakfast, free parking, and a casino. Our guests praise the clean rooms in our reviews. Popular attractions ...
Hampton Inn McHenry

Hampton Inn McHenry

2.5 out of 5
1555 South Route 31 McHenry IL
30.99 km from city center
Stay at this hotel in McHenry. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions McHenry ...
Extended Stay America Suites Chicago Elgin West Dundee

Extended Stay America Suites Chicago Elgin West Dundee

2.5 out of 5
2185 Marriott Dr West Dundee IL
20.2 km from city center
Book a stay at this business-friendly hotel in West Dundee. Enjoy free breakfast, free parking, and a 24-hour fitness center. Popular attractions Santa's Village ...
Holiday Inn Chicago Northwest-Elgin by IHG

Holiday Inn Chicago Northwest-Elgin by IHG

3 out of 5
495 Airport Rd Elgin IL
20.08 km from city center
Book a stay at this business-friendly hotel in Elgin. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
Quality Inn and Suites St Charles - West Chicago

Quality Inn and Suites St Charles - West Chicago

2.5 out of 5
1600 E Main St St. Charles IL
27.98 km from city center
Book a stay at this business-friendly hotel in St. Charles. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Red Roof Inn PLUS+ Chicago - Hoffman Estates

Red Roof Inn PLUS+ Chicago - Hoffman Estates

2.5 out of 5
2500 Hassell Road Hoffman Estates IL
32.29 km from city center
Book a stay at this business-friendly hotel in Hoffman Estates. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff ...
Geneva Motel Inn

Geneva Motel Inn

2 out of 5
100 South Tyler Rd St. Charles IL
28.06 km from city center
Book a stay at this business-friendly hotel in St. Charles. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
Chicago Marriott Northwest

Chicago Marriott Northwest

3.5 out of 5
4800 Hoffman Blvd Hoffman Estates IL
27.78 km from city center
Book a stay at this business-friendly hotel in Hoffman Estates. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff ...
Country Inn & Suites by Radisson, Crystal Lake, IL

Country Inn & Suites by Radisson, Crystal Lake, IL

2.5 out of 5
600 Tracy Trail Crystal Lake IL
24.06 km from city center
Stay at this hotel in Crystal Lake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Best Western Plus Elgin - Chicago

Best Western Plus Elgin - Chicago

3 out of 5
2175 Marriott Dr West Dundee IL
20.12 km from city center
Book a stay at this business-friendly hotel in West Dundee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Comfort Suites Elgin

Comfort Suites Elgin

2.5 out of 5
2480 Bushwood Drive Elgin IL
15.93 km from city center
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. ...
Don't see what you're looking for?
See all available properties in Hampshire
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Wed, Mar 18 - Tue, Mar 31
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$140 Roundtrip, found 4 days ago
$140
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Mar 18 from Los Angeles Intl. to O'Hare Intl., returning Tue, Mar 31, priced at $140 found 4 days ago
Spirit Airlines
Thu, May 7 - Tue, May 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$188 Roundtrip, found 3 days ago
$188
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Thu, May 7 from Los Angeles Intl. to O'Hare Intl., returning Tue, May 19, priced at $188 found 3 days ago
United
Mon, Jan 5 - Mon, Jan 12
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$695 Roundtrip, found 14 hours ago
$695
Roundtrip
found 14 hours ago
Select United flight, departing Mon, Jan 5 from Los Angeles Intl. to O'Hare Intl., returning Mon, Jan 12, priced at $695 found 14 hours ago
American Airlines
Mon, Jan 5 - Mon, Jan 12
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$777 Roundtrip, found 14 hours ago
$777
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Mon, Jan 5 from Los Angeles Intl. to O'Hare Intl., returning Mon, Jan 12, priced at $777 found 14 hours ago
Alaska Airlines
Mon, Jan 5 - Mon, Jan 12
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$788 Roundtrip, found 14 hours ago
$788
Roundtrip
found 14 hours ago
Select Alaska Airlines flight, departing Mon, Jan 5 from Los Angeles Intl. to O'Hare Intl., returning Mon, Jan 12, priced at $788 found 14 hours ago