Search Deals onWinnetka Vacation Packages
Winnetka Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Kinzie Hotel
Save 100% on your flight
Price was $708, price is now $453 per person
$453
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
We had such a wonderful stay at The Kinzie Hotel in Chicago! ❤️
My girlfriend and I were there for a little girls’ getaway, and honestly, the hotel was the perfect choice. The location was fantastic — we could walk to so many restaurants, shops and things we wanted to do. Our room was comfortable and clean, and the staff couldn’t have been nicer or more helpful.
We had so much fun exploring Chicago, eating our way around the city 😂, and seeing Dirty Dancing! Coming back to The Kinzie at the end of the day felt like coming home.
We absolutely loved our stay and would 100% stay at The Kinzie again! Highly recommend!
Reviewed on Sep 14, 2026
Kimpton Gray Hotel by IHG
Save 100% on your flight
Price was $1,056, price is now $595 per person
$595
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
The Talbott, Autograph Collection
Save 100% on your flight
Price was $992, price is now $572 per person
$572
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury 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 Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $1,671, price is now $1,010 per person
$1,010
per person
Nov 24 - Nov 28
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.
One of the best hotels in the city, I would do it over again in the blink of an eye
Reviewed on Sep 14, 2026
Level Chicago – Old Town
Save 100% on your flight
Price was $1,325, price is now $818 per person
$818
per person
Nov 4 - Nov 9
found 24 hours 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
Save 100% on your flight
Price was $750, price is now $463 per person
$463
per person
Dec 9 - Dec 13
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.
It was a very nice hotel and everyone was extremely helpful!!
Reviewed on Sep 14, 2026
Swissotel - Chicago
Save 100% on your flight
Price was $814, price is now $516 per person
$516
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Emily Hotel
Save 100% on your flight
Price was $922, price is now $588 per person
$588
per person
Nov 18 - Nov 22
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.
Comfortable room with a great view and luxuriously soft bed!
Reviewed on Sep 13, 2026
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.
Wed, Oct 14 - Sat, Oct 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 4 days ago
$100
Roundtrip
found 4 days ago
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$215 Roundtrip, found 1 hour ago
$215
Roundtrip
found 1 hour ago
Mon, Oct 5 - Tue, Oct 6
LAX
Los Angeles Intl.
MDW
Midway Intl.
$261 Roundtrip, found 5 hours ago
$261
Roundtrip
found 5 hours ago
Fri, Nov 13 - Mon, Nov 30
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,164 Roundtrip, found 1 day ago
$1,164
Roundtrip
found 1 day ago
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