Search Deals onWinnetka Vacation Packages
Winnetka Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $661, price is now $426 per person
$426
per person
Dec 18 - Dec 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 breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Súper cerca a todas las atracciones de Chicago
Reviewed on Oct 12, 2026
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $1,252, price is now $720 per person
$720
per person
Nov 12 - Nov 15
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.
Great location
Reviewed on Oct 12, 2026
The Emily Hotel
Save 100% on your flight
Price was $866, price is now $534 per person
$534
per person
Dec 22 - Dec 27
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.
The staff is super nice and great amenities
Reviewed on Oct 11, 2026
Level Chicago Fulton Market
Save 100% on your flight
Price was $739, price is now $461 per person
$461
per person
Dec 8 - Dec 12
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Swissotel - Chicago
Save 100% on your flight
Price was $761, price is now $478 per person
$478
per person
Dec 18 - Dec 22
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.
Level Chicago – Old Town
Save 100% on your flight
Price was $919, price is now $582 per person
$582
per person
Dec 18 - Dec 22
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 stay was all good as represented on the site!
Reviewed on Oct 12, 2026
Kimpton Gray Hotel by IHG
Save 100% on your flight
Price was $797, price is now $522 per person
$522
per person
Dec 22 - Dec 27
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.
Great location awesome hotel
Reviewed on Oct 13, 2026
JW Marriott Chicago
Save 100% on your flight
Price was $749, price is now $497 per person
$497
per person
Nov 12 - Nov 15
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, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Perfect location
Reviewed on Oct 12, 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.
Thu, Nov 12 - Fri, Nov 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 3 hours ago
$197
Roundtrip
found 3 hours ago
Wed, Nov 11 - Fri, Nov 13
LAX
Los Angeles Intl.
MDW
Midway Intl.
$197 Roundtrip, found 12 hours ago
$197
Roundtrip
found 12 hours ago
Thu, Nov 12 - Fri, Nov 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 3 hours ago
$197
Roundtrip
found 3 hours ago
Fri, Nov 13 - Wed, Dec 2
PVG
Pudong Intl.
ORD
O'Hare Intl.
$998 Roundtrip, found 21 hours ago
$998
Roundtrip
found 21 hours ago
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