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Winthrop Harbor Vacation Packages

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A sunset over a calm sea with a rocky foreground and a row of poles in the distance.

Winthrop Harbor
Illinois
United States of America
North America
Hotwire.com

Winthrop Harbor Flight + Hotel Packages

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

Hotel Felix River North/Magnificent Mile

4 out of 5

Price was $507, price is now $338 per person

$338

per person

Jan 28 - Feb 3

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.

Very clean. Had everything that we needed

Reviewed on Nov 10, 2026

Hotel Riu Plaza Chicago

4 out of 5

Price was $806, price is now $491 per person

$491

per person

Jan 28 - Feb 3

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.

Clean and nice enjoy the weekend

Reviewed on Nov 10, 2026

Swissotel - Chicago

4.5 out of 5

Price was $1,305, price is now $815 per person

$815

per person

Jan 28 - Feb 3

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.

Everything very nice it is centered where u can go to a lot of attractions

Reviewed on Nov 10, 2026

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 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.

Le Méridien Essex Chicago

4 out of 5

Price was $713, price is now $453 per person

$453

per person

Jan 28 - Feb 3

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, room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.

I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything.

Reviewed on Nov 3, 2026

Eurostars Magnificent Mile

4 out of 5

Price was $691, price is now $457 per person

$457

per person

Jan 28 - Feb 3

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.

Reviewed on Nov 10, 2026

Pendry Chicago

4.5 out of 5

Price was $704, price is now $483 per person

$483

per person

Jan 28 - Jan 31

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.

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

Hotel Saint Clair- Magnificent Mile

4 out of 5

Price was $700, price is now $482 per person

$482

per person

Jan 28 - Feb 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

Stay at this 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.

It was nice, however it is unfortunate there is only two elevators and they are tiny. There is over 14 floors and I believe only one ice machine/vending machine only on 2nd floor.

Reviewed on Nov 10, 2026

Winthrop Harbor Vacation Packages 3-4 Night Stays

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

Le Méridien Essex Chicago

4 out of 5

Downtown Chicago

Price was $473, price is now $330 per person

$330

per person

Jan 28 - Jan 31

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

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 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)