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Winnetka Vacation Packages

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Winnetka Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago

Hilton Chicago

4 out of 5
Save 100% on your flight
Price was $515, price is now $315 per person
$315
per person
Mar 11 - Mar 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Soldier Field are located nearby.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
Price was $612, price is now $316 per person
$316
per person
Mar 11 - Mar 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, 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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $694, price is now $385 per person
$385
per person
Mar 11 - Mar 14
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.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $628, price is now $354 per person
$354
per person
Apr 3 - Apr 6
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $964, price is now $555 per person
$555
per person
Mar 11 - Mar 14
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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $594, price is now $347 per person
$347
per person
Mar 11 - Mar 14
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.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $733, price is now $431 per person
$431
per person
Mar 11 - Mar 14
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, 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $582, price is now $345 per person
$345
per person
Mar 11 - Mar 14
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.

Winnetka Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $612, price is now $316 per person
$316
per person
Mar 11 - Mar 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $694, price is now $385 per person
$385
per person
Mar 11 - Mar 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $628, price is now $354 per person
$354
per person
Apr 3 - Apr 6
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $964, price is now $555 per person
$555
per person
Mar 11 - Mar 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Winnetka Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $723, price is now $359 per person
$359
per person
Mar 19 - Mar 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $788, price is now $421 per person
$421
per person
Mar 19 - Mar 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $917, price is now $499 per person
$499
per person
Mar 19 - Mar 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $889, price is now $495 per person
$495
per person
Mar 19 - Mar 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Tue, Mar 17 - Tue, Mar 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$140 Roundtrip, found 5 days ago
$140
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Mar 17 from Los Angeles Intl. to O'Hare Intl., returning Tue, Mar 24, priced at $140 found 5 days ago
Frontier Airlines
Thu, Feb 12 - Sat, Feb 21
LAX
Los Angeles Intl.
MDW
Midway Intl.
$190 Roundtrip, found 23 hours ago
$190
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Thu, Feb 12 from Los Angeles Intl. to Midway Intl., returning Sat, Feb 21, priced at $190 found 23 hours ago
American Airlines
Fri, Jan 9 - Sun, Jan 11
LAX
Los Angeles Intl.
RFD
Greater Rockford
$571 Roundtrip, found 6 days ago
$571
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Jan 9 from Los Angeles Intl. to Greater Rockford, returning Sun, Jan 11, priced at $571 found 6 days ago
All Nippon Airways
Wed, Mar 4 - Mon, Mar 16
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,144 Roundtrip, found 2 days ago
$1,144
Roundtrip
found 2 days ago
Select All Nippon Airways flight, departing Wed, Mar 4 from Pudong Intl. to O'Hare Intl., returning Mon, Mar 16, priced at $1,144 found 2 days ago