
Winthrop Harbor Vacations from $461
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The Latest Winthrop Harbor vacation packages
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $769, price is now $461 per person
$461
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,809 reviews)
Clean, cozy, and updated. The shampoo and conditioner was amazing!! Consider selling it to guests!
Reviewed on Jul 12, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,319, price is now $799 per person
$799
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
The floor in the room was not clean. The shower gel was empty. The bed was comfortable and the breakfast buffet was good
Reviewed on Jul 11, 2026


Residence Inn by Marriott Chicago Bloomingdale
Save 100% on your flight
Price was $764, price is now $476 per person
$476
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (383 reviews)
Staff was welcoming. Continental breakfast was above average. We stayed in a 2bdr/2ba suite and just had a couple of minor annoyances with the room. The shower head was seemingly broken and there was cardboard folded and wedged in so that it would stay on the rod. If you touched it at all, it'd just fall off. The sink sprayer also did not stay up at the base of the faucet - it just dangled there in the sink. It made it a slight pain to do dishes. Neither problem was the end of the world, but attention to detail and the little things can be impacted.
Upon checking in (stayed Wed-Mon), we had asked for room cleanings (towels, bedding, and trash) for Friday and Sunday. They only did that Friday. We had to call the front desk for towels ourselves after getting back to the room from a full day of being in 100 degree weather and sweating to find we had no clean laundry.
Again, not the end of the world but it caused disappointment after having a much better experience there the year prior.
Reviewed on Jul 7, 2026

Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
Price was $958, price is now $600 per person
$600
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Staff was amazing, we had a single king bed corner suite with a separate room that has a pull out bed from the couch. It was a perfect setup for us because the kids had their own little room with their own tv and everything. The pullout couch bed was very uncomfortable, but we kinda figured it wouldn't be the best in the first place so that was alright. The king bed was pretty good, no complaints there... What we disliked was that the room was not properly cleaned before us. They didn't vacuum, there were beer caps and change on the floor. The toilet was for sure not cleaned after the last guests in the room because it was pretty bad. There were only two bath towels which wasn't a big deal cause they brought us more and they also brought us a microwave after asking, that was pretty nice. The really stupid thing with the king bed room was that the TV is literally all the way over to the left mounted on the wall where you couldn't see it very well while laying in bed... It is really really stupid if you see what im talking about here. Imagine laying in bed at a $300 a night hotel and you and your wife are trying to watch a TV thats WAY over on the left side of the room... Its actually comical how the set up is... Valet parking is insane at $90 a night so I would recommend finding parking elsewhere around the hotel if you can. Overall it was a OK stay, nothing incredible and definitely not worth the $300 plus $90 parking...
Reviewed on Jul 12, 2026
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Winthrop Harbor Hotel Deals

LA VILLA MOTEL
1401 Sheridan Rd Winthrop Harbor IL
Fully refundable
$61 nightly
The price is $71 total per night from Jul 20 to Jul 21
$71 total
Jul 20 - Jul 21
Total with taxes and fees
6.8/10 (73 reviews)
"Dirty and moldy"
Reviewed on Jun 30, 2026

Motel Sun Inn
301 Sheridan Road Winthrop Harbor IL
Fully refundableReserve now, pay when you stay
$73 nightly
The price is $85 total per night from Jul 13 to Jul 14
$85 total
Jul 13 - Jul 14
Total with taxes and fees
7/10 Good! (282 reviews)
"The staff were so nice! The rooms and bathroom were so clean. The building is a little older but everything was in good shape. Free WiFi use and the air conditioner worked perfectly. The price was also fair. It was 90 dollars and a 50 dollar deposit fee but you get the 50 dollars back in your account ..."
Reviewed on Jun 25, 2026

Great Wolf Lodge Illinois
1700 Nations Dr Gurnee IL
$169 nightly
The price is $193 total per night from Aug 9 to Aug 10
$193 total
Aug 9 - Aug 10
Total with taxes and fees
8.6/10 Excellent! (1,018 reviews)
"Went with my grandson and had an amazing we had such a great time we will be back again"
Reviewed on Jul 11, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find the Best Winthrop Harbor Vacation Packages
Winthrop Harbor Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 6,800 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
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