Downtown Vacations from $303
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The Latest Downtown Vacation Packages
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $503, price is now $303 per person
$303
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.
Reviewed on Dec 8, 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $623, price is now $377 per person
$377
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
The rooms were great. Very spacious, fully stocked kitchen and extremely clean. We loved having access to the 8th floor with the steam room, sauna, fitness center, game rooms, and socializing areas 24/7. Would love to experience it in the summer with the pool and outdoor areas. We were also fortunate enough to attend during their Christmas Brunch buffet which was such a great perk! If the price stays around the same, I will continue to stay at Level hotels exclusively in any cities I visit that has one! I’ve already told so many people about my wonderful hotel experience.
Reviewed on Dec 9, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $597, price is now $362 per person
$362
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
All of the above. Staff was wonderful. Room was clean and comfortable. On site amenities were great and food was superb. Best espresso martini I’ve ever tasted.
Reviewed on Dec 11, 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $578, price is now $353 per person
$353
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Very pleasant stay for my birthday! Will definitely come back and recommend to others! Top notch service and rooms were beautiful and comfortable!
Reviewed on Dec 13, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $622, price is now $381 per person
$381
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Concierge not helpful and neither is was the door man,
Neither would get me a cab, they said to just stand outside
Reviewed on Dec 4, 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 North Beach and Michigan Maritime Museum.
Downtown Hotel Deals
Old Harbor Inn
515 Williams Street South Haven MI
$144 nightly
The price is $160 total per night from Dec 16 to Dec 17
$160 total
Dec 16 - Dec 17
Total with taxes and fees
9.4/10 Exceptional! (680 reviews)
Great location
Reviewed on Dec 14, 2025
Historic Hotel Nichols
201 Center St South Haven MI
$118 nightly
The price is $131 total per night from Dec 18 to Dec 19
$131 total
Dec 18 - Dec 19
Total with taxes and fees
9.6/10 Exceptional! (125 reviews)
Love the location, hospitality and uniqueness of this historic hotel located downtown and within walking distance of shops and restaurants. A welcome haven (in South Haven) from status quo highway hotels.
Reviewed on Dec 8, 2025
New Home with swim spa, theatre & game room. 1 block to town & close to beach.
South Haven MI
10/10 Exceptional! (195 reviews)
I only gave this property and host 5 stars because there was not a higher rating. Susan was amazing very communicative and friendly. She made this stay very comfortable and one of the most amazing properties I have ever experienced. The house has enough entertainment options even if your not able ...
Reviewed on Nov 23, 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.