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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 Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Save 100% on your flight
Price was $357, price is now $221 per person
$221
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $807, price is now $476 per person
$476
per person
Feb 20 - Feb 23
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 Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $558, price is now $337 per person
$337
per person
Feb 20 - Feb 23
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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $485, price is now $297 per person
$297
per person
Feb 20 - Feb 23
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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $457, price is now $287 per person
$287
per person
Feb 20 - Feb 23
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 $640, price is now $404 per person
$404
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $448, price is now $283 per person
$283
per person
Feb 20 - Feb 23
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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
Price was $372, price is now $238 per person
$238
per person
Feb 6 - Feb 8
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.

Winnetka Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $457, price is now $287 per person
$287
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $807, price is now $476 per person
$476
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $558, price is now $337 per person
$337
per person
Feb 20 - Feb 23
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 $485, price is now $297 per person
$297
per person
Feb 20 - Feb 23
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 $610, price is now $344 per person
$344
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $687, price is now $381 per person
$381
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $864, price is now $482 per person
$482
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $724, price is now $407 per person
$407
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)

Top Flight Deals

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

Frontier Airlines
Sat, Feb 7 - Sun, Feb 8
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$158 Roundtrip, found 1 day ago
$158
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Feb 7 from Los Angeles Intl. to O'Hare Intl., returning Sun, Feb 8, priced at $158 found 1 day ago
Delta
Wed, Jan 7 - Wed, Jan 14
LAX
Los Angeles Intl.
MDW
Midway Intl.
$217 Roundtrip, found 6 days ago
$217
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jan 7 from Los Angeles Intl. to Midway Intl., returning Wed, Jan 14, priced at $217 found 6 days ago
American Airlines
Fri, Jan 9 - Sun, Jan 11
LAX
Los Angeles Intl.
RFD
Greater Rockford
$400 Roundtrip, found 2 days ago
$400
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Jan 9 from Los Angeles Intl. to Greater Rockford, returning Sun, Jan 11, priced at $400 found 2 days ago
Icelandair
Sat, Dec 13 - Mon, Dec 15
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$750 Roundtrip, found 1 day ago
$750
Roundtrip
found 1 day ago
Select Icelandair flight, departing Sat, Dec 13 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Mon, Dec 15, priced at $750 found 1 day ago