Downtown Vacations from $248
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The Latest Downtown Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $437, price is now $248 per person
$248
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,188 reviews)
Floor-to- ceiling windows providing beautiful views of the Lake and City skyline (and windowseat) were very nice. Location was nice. Room was quiet. Bed was very comfortable. Staff was courteous and helpful.
Reviewed on Oct 28, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $520, price is now $281 per person
$281
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Our stay was absolutely excellent! The room was spotless and stylish, but what really stood out was the rooftop — breathtaking views, great ambiance, and the perfect spot to unwind. The concierge team was phenomenal — attentive, knowledgeable, and made every recommendation feel personalized. From check-in to check-out, everything felt seamless and top-tier. Truly a 5-star experience worth repeating!
Reviewed on Oct 28, 2025
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was $962, price is now $539 per person
$539
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (721 reviews)
Room was very dirty, had to purchase cleaning supplies to clean floors, restrooms and wash all sheets. Would not book this location again.
Reviewed on Oct 29, 2025
Doubletree Hotel South Bend
Downtown South Bend
Price was $1,310, price is now $737 per person
$737
per person
Dec 15 - Dec 18
found 8 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to South Bend (SBN)
7.6/10 Good! (1,015 reviews)
Room was OK but the fitness center needs a major renovation- smelled as if a homeless person was living there for weeks.
Reviewed on Oct 20, 2025
Where to stay in Downtown
Find the best Downtown areas and neighborhoods for the activities you enjoy most. Learn more about Downtown
North Side
1 out of top 10 points of interest in this area
While visiting North Side, you might make a stop by sights like Michigan Maritime Museum and North Beach.
Downtown Hotel Deals
Old Harbor Inn
515 Williams Street, South Haven, MI
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $146 total per night from Oct 30 to Oct 31
$146 total
Oct 30 - Oct 31
Total with taxes and fees
9.4/10 Exceptional! (663 reviews)
Room was very clean and the staff was very friendly
Reviewed on Oct 26, 2025
Historic Hotel Nichols
201 Center St, South Haven, MI
$155 nightly
The price is $172 total per night from Nov 25 to Nov 26
$172 total
Nov 25 - Nov 26
Total with taxes and fees
9.6/10 Exceptional! (120 reviews)
We had a wonderful visit.
Reviewed on Oct 20, 2025
Amazing in ground Pool, 5 bedroom 3 bath, Short Walk to Town and Beach
South Haven
9.8/10 Exceptional! (54 reviews)
The house, pool, and location were all just perfect for a ladies get-a-way! Mother Nature cooperated and gave us a beautiful weather weekend so we were able to enjoy the pool and gas fire pit. The house was very well stocked with everything you could imagine and so clean (and I’m a bit fussy about ...
Reviewed on Sep 28, 2025
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.
Discover the most popular places to visit in Downtown
Kal Haven Trail
You can take time to visit Kal Haven Trail during your travels to South Haven. While you're in the area, stroll along the beautiful beaches.
South Haven Center for the Arts
5/5(1 review)
Explore the campus of South Haven Center for the Arts as part of your travels around South Haven. While you're in the area, stroll along the beautiful beaches.
Warner Vineyards
3/5(1 review)
You can enjoy a tasting or tour at Warner Vineyards during your travels to South Haven. While you're in the area, stroll along the beautiful beaches.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.