Deals on vacations and trips to Winnetka
Save when you book Winnetka package deals
Winnetka flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $308, price is now $150 per person
$150
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Limo/town car service, WiFi in public areas, and express check-out are also on offer.
The Westin Michigan Avenue Chicago
Downtown Chicago
Price was $1,201, price is now $535 per person
$535
per person
Dec 23 - Dec 27
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $384, price is now $196 per person
$196
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.
Holiday Inn Chicago - Schaumburg by IHG
Save 100% on your flight
Price was $447, price is now $237 per person
$237
per person
Dec 26 - Dec 31
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free parking, a snack bar/deli, and a computer station are also offered.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $493, price is now $263 per person
$263
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.
Top Winnetka hotels deals
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
$87 nightly
The price is $102 total per night
$102 total
Dec 8 - Dec 9
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.
Pool
Breakfast included
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$131 nightly
The price is $149 total per night
$149 total
Nov 25 - Nov 26
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and limo/town car service.
Pool
Spa
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Free Cancellation
Reserve now, pay when you stay
$83 nightly
The price is $98 total per night
$98 total
Dec 7 - Dec 8
Total with taxes and fees
A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.
Pet friendly
Free WiFi
citizenM Chicago Downtown
80 East Wacker Place Chicago IL
Free Cancellation
Reserve now, pay when you stay
$117 nightly
The price is $137 total per night
$137 total
Nov 25 - Nov 26
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, a communal living room, and express check-in are also on offer.
Free WiFi
Restaurant
Warwick Allerton - Chicago
701 North Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $100 total per night
$100 total
Dec 16 - Dec 17
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Families will appreciate the onsite laundry facilities and babysitting. WiFi in public areas is free.
Free WiFi
Air conditioning
The Whitehall Hotel, BW Premier Collection
105 E Delaware Pl Chicago IL
Free Cancellation
Reserve now, pay when you stay
$87 nightly
The price is $103 total per night
$103 total
Nov 25 - Nov 26
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.
Breakfast included
Pet friendly
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.
Popular places to visit
Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
4.5/5(332 reviews)
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
McCormick Place
4.5/5(1,805 reviews)
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
Frequently asked questions
Photos of local treasures
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