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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.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Price was $644, price is now $452 per person
$452
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Price was $910, price is now $574 per person
$574
per person
Jan 23 - Jan 27
found 4 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.

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was $725, price is now $486 per person
$486
per person
Jan 22 - Jan 25
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.
Price to high for the quality.

Reviewed on Nov 9, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Price was $815, price is now $555 per person
$555
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 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.
Everything really nice rooms and the view was amazing !!

Reviewed on Nov 9, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Price was $704, price is now $483 per person
$483
per person
Jan 28 - Jan 31
found 23 hours 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.
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.

Reviewed on Nov 8, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Price was $1,054, price is now $754 per person
$754
per person
Jan 22 - Jan 25
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.
Staff was very inviting and courteous. Room was clean. Valet was very very kind and prompt. I cannot say enough great things about the valet associates. They were very friendly.

Reviewed on Nov 9, 2026

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Price was $1,051, price is now $764 per person
$764
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 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
Price was $2,050, price is now $1,501 per person
$1,501
per person
Dec 23 - Dec 29
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.
Very good service

Reviewed on Nov 9, 2026

Winnetka Vacation Packages 3-4 Night Stays

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

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $704, price is now $483 per person
$483
per person
Jan 28 - Jan 31
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was $910, price is now $574 per person
$574
per person
Jan 23 - Jan 27
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $725, price is now $486 per person
$486
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was $815, price is now $555 per person
$555
per person
Jan 22 - Jan 25
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.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was $713, price is now $453 per person
$453
per person
Jan 28 - Feb 3
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $806, price is now $491 per person
$491
per person
Jan 28 - Feb 3
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was $1,305, price is now $815 per person
$815
per person
Jan 28 - Feb 3
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $1,390, price is now $871 per person
$871
per person
Dec 24 - Dec 31
just found
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, Dec 8 - Thu, Dec 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$161 Roundtrip, found 13 hours ago
$161
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Tue, Dec 8 from Los Angeles Intl. to O'Hare Intl., returning Thu, Dec 17, priced at $161 found 13 hours ago
Frontier Airlines
Thu, Dec 17 - Fri, Dec 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$238 Roundtrip, found 14 hours ago
$238
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Thu, Dec 17 from Los Angeles Intl. to O'Hare Intl., returning Fri, Dec 18, priced at $238 found 14 hours ago
Southwest Airlines
Tue, Jan 5 - Tue, Jan 19
LAX
Los Angeles Intl.
MDW
Midway Intl.
$247 Roundtrip, found 14 hours ago
$247
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Tue, Jan 5 from Los Angeles Intl. to Midway Intl., returning Tue, Jan 19, priced at $247 found 14 hours ago
Air Canada
Fri, Nov 13 - Mon, Nov 30
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,174 Roundtrip, found 1 day ago
$1,174
Roundtrip
found 1 day ago
Select Air Canada flight, departing Fri, Nov 13 from Pudong Intl. to O'Hare Intl., returning Mon, Nov 30, priced at $1,174 found 1 day ago