Search Deals onWinnetka Vacation Packages
Winnetka Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Price was $367, price is now $255 per person
$255
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
I hate not being able to make coffee in my room, hate to get dressed to go down stairs to get coffee
Reviewed on Oct 13, 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 – 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
Level Chicago Fulton Market
Save 100% on your flight
Price was $798, price is now $522 per person
$522
per person
Dec 25 - Dec 29
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 a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Pendry Chicago
Save 100% on your flight
Price was $833, price is now $552 per person
$552
per person
Dec 3 - Dec 6
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.
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $960, price is now $662 per person
$662
per person
Nov 13 - 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 Talbott, Autograph Collection
Save 100% on your flight
Price was $801, price is now $556 per person
$556
per person
Nov 13 - 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, 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.
Dorothy's
Save 100% on your flight
Price was $377, price is now $266 per person
$266
per person
Dec 15 - Dec 19
just found
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this B&B in Chicago. Enjoy free breakfast, free WiFi, and housekeeping. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
Dorothy's is a nice place for people wanting easy access to a clean, SRO-style room in a good location with an invisible staff (online checkin).
Specific complaints: my room lacked both trash can and bedside light.
And the self-serve breakfast provided nice individual portions of yogurt and bags of nuts, but on neither morning was coffee available (happily there are places only blocks away to buy some).
Plus, charging extra for checking in 1-3-hours earlier than the 4pm check-in seems a little tacky (I've been traveling for many decades and never confronted this add-on).
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, just found
$197
Roundtrip
just found
Wed, Nov 11 - Fri, Nov 13
LAX
Los Angeles Intl.
MDW
Midway Intl.
$197 Roundtrip, found 9 hours ago
$197
Roundtrip
found 9 hours ago
Thu, Nov 12 - Fri, Nov 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, just found
$197
Roundtrip
just found
Fri, Nov 13 - Wed, Dec 2
PVG
Pudong Intl.
ORD
O'Hare Intl.
$998 Roundtrip, found 19 hours ago
$998
Roundtrip
found 19 hours ago
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