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Winthrop Harbor Vacation Packages

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Winthrop Harbor Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was $425, price is now $306 per person
$306
per person
Dec 10 - Dec 13
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.

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 1 hour 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.
The staff were more ghan helpful even when checking in after midnight The room was very spacious and clean The breakfast selection catered for everyone with good quality food foe everyone Had a wonderful stay, could not find a fault Thank you for your hospitality during our stsy

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.

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 20 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

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Price was $611, price is now $433 per person
$433
per person
Dec 10 - 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 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.

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.
The service here was amazing. I highly would recommend this to my friends and family. I can’t wait to stay here again.

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.

Winthrop Harbor 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 20 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 1 hour 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)

Winthrop Harbor 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 20 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 20 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 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was $691, price is now $457 per person
$457
per person
Jan 28 - Feb 3
found 20 hours ago
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 10 hours ago
$161
Roundtrip
found 10 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 10 hours ago
Frontier Airlines
Thu, Dec 17 - Fri, Dec 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$238 Roundtrip, found 11 hours ago
$238
Roundtrip
found 11 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 11 hours ago
United
Tue, Dec 29 - Wed, Jan 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$247 Roundtrip, found 6 hours ago
$247
Roundtrip
found 6 hours ago
Select United flight, departing Tue, Dec 29 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jan 6, priced at $247 found 6 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