Search Deals onWinnetka Vacation Packages
Winnetka Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Blue Chip Casino Hotel and Spa
Save 100% on your flight
Price was $400, price is now $255 per person
$255
per person
Nov 17 - Nov 21
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Stay at this 3.5-star spa hotel in Michigan City. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Blue Chip Casino and Hanson Park are located nearby.

The Emily Hotel
Price was $1,466, price is now $748 per person
$748
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly 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 United Center and Chicago Riverwalk are located nearby.

Chicago Athletic Association, a Hyatt Hotel
Save 100% on your flight
Price was $913, price is now $537 per person
$537
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Arlo Chicago
Save 100% on your flight
Price was $775, price is now $459 per person
$459
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Hotel Felix River North/Magnificent Mile
Save 100% on your flight
Price was $552, price is now $329 per person
$329
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.

Hilton Chicago O'Hare Airport
Save 100% on your flight
Price was $1,012, price is now $614 per person
$614
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and The Dome at the Parkway Bank Sports Complex are located nearby.

Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $782, price is now $477 per person
$477
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Eurostars Magnificent Mile
Save 100% on your flight
Price was $922, price is now $575 per person
$575
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
Winnetka Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Winnetka 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.

Sat, Sep 13 - Sat, Sep 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$127 Roundtrip, found 4 days ago
$127
Roundtrip
found 4 days ago

Thu, Sep 25 - Thu, Oct 2
LAX
Los Angeles Intl.
MDW
Midway Intl.
$179 Roundtrip, found 20 hours ago
$179
Roundtrip
found 20 hours ago

Fri, Sep 5 - Sun, Sep 7
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$550 Roundtrip, found 4 days ago
$550
Roundtrip
found 4 days ago

Mon, Sep 22 - Sat, Oct 4
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$853 Roundtrip, found 4 days ago
$853
Roundtrip
found 4 days ago
Discover Other Travel Deals
- Home Alone House Vacations
- Chocolate Box Vacations
- Wrigley Field Vacations
- Naval Base Great Lakes Vacations
- Michigan Avenue Vacations
- Navy Pier Vacations
- McCormick Place Vacations
- Millennium Park Vacations
- Soldier Field Vacations
- Grant Park Vacations
- Chicago Riverwalk Vacations
- Lake Michigan Vacations
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations