Find Romantic Hotels in Crestwood, IL from $86

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Check availability on Crestwood Romantic Hotels

Our top choices for Crestwood romantic hotels

Aloft Chicago Mag Mile

3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2956)
"Great location and great staff!!"
United States
lynne
$77 nightly
The price is $90
Dec 10 - Dec 11
Total with taxes and fees
Aloft Chicago Mag Mile

Eurostars Magnificent Mile

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3135)
"Amazing and will be staying again!"
United States
Angie
$94 nightly
The price is $110
Jan 8 - Jan 9, 2026
Total with taxes and fees
Eurostars Magnificent Mile

Warwick Allerton - Chicago

4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (3009)
"Enjoyed this hotel stay. "
United States
Kimberly
$95 nightly
The price is $111
Dec 18 - Dec 19
Total with taxes and fees
Warwick Allerton - Chicago

The Godfrey Hotel Chicago

4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1919)
"Good value, great cleaning staff "
United Kingdom
farzana
$115 nightly
The price is $135
Jan 6 - Jan 7, 2026
Total with taxes and fees
The Godfrey Hotel Chicago

Silversmith Hotel Chicago Downtown

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2108)
"Great hotel. Very affordable for such a perfect location."
United States
Nicholas
$127 nightly
The price is $149
Jan 4 - Jan 5, 2026
Total with taxes and fees
Silversmith Hotel Chicago Downtown

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (2749)
"Great food clean room friendly staff"
United States
MARINA
$110 nightly
The price is $129
Jan 6 - Jan 7, 2026
Total with taxes and fees
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Hilton Chicago/Magnificent Mile Suites

3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3453)
"Great place to stay "
United States
RaShawna
$106 nightly
The price is $124
Dec 17 - Dec 18
Total with taxes and fees
Hilton Chicago/Magnificent Mile Suites

Hotel Saint Clair- Magnificent Mile

4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (1788)
"Great stay in a great area."
United States
Giselle
$74 nightly
The price is $86
Dec 11 - Dec 12
Total with taxes and fees
Hotel Saint Clair- Magnificent Mile

Millennium Knickerbocker Chicago

4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2003)
"Great location, clean hotel"
United States
Andre
$109 nightly
The price is $128
Jan 4 - Jan 5, 2026
Total with taxes and fees
Millennium Knickerbocker Chicago

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2265)
"Smooth check in and beautiful hotel"
United States
Monique
$119 nightly
The price is $139
Dec 16 - Dec 17
Total with taxes and fees
Sable at Navy Pier Chicago, Curio Collection by Hilton
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 out more about Crestwood

Crestwood attractions for couples

Crestwood, Illinois offers a blend of family-friendly activities and local charm that will surely delight quality-seeking travelers. Start your adventure at the Rainbow Falls Waterpark, where both kids and adults can splash around in a vibrant aquatic playground featuring slides, a lazy river, and a relaxing pool area. For a taste of nature, visit the nearby Crestwood Park, which boasts walking trails, playgrounds, and picnic spots, ideal for a family day out. If you’re a sports enthusiast, catch a game at the nearby Toyota Park, home to the Chicago Fire soccer team, where the electric atmosphere will have you cheering along with fellow fans. Foodies will appreciate the diverse dining options, from local pizzerias to family-style restaurants, serving delicious meals that cater to every palate. After a day of exploration, consider staying in the cozy hotels located near the bustling Cicero Avenue, where you'll find comfortable accommodations that prioritize guest service, ensuring your family feels pampered during your stay. Enjoy the convenience of being close to shopping and entertainment, and relish the peace of mind that comes from knowing you've chosen quality amenities for a memorable trip.

Find the best romantic hotels in Crestwood

For couples seeking a charming getaway in Crestwood, Illinois, these hotels offer a cozy atmosphere perfect for romance. Enjoy comfortable stays with inviting amenities that enhance your experience together.

Holiday Inn Express Crestwood by IHG

  • Why it's great for a couples retreat: The Holiday Inn Express Crestwood by IHG is a great choice for couples looking for a comfortable and affordable stay. With a solid guest review rating of 7.8, it provides a cozy environment where guests can unwind after a day of exploring. While it may not feature specific romantic amenities, its inviting indoor pool and complimentary breakfast create a pleasant atmosphere for couples to enjoy a leisurely morning together.
  • Other amenities: Additional amenities include free off-street parking, daily housekeeping, and a fitness center to keep up with workouts. Guests can also make use of in-room conveniences like a microwave and sofa beds, adding to the comfort of their stay. With easy access to local attractions, this hotel offers the perfect base for a romantic escape.
  • Nearby attractions: Hollywood Park - 0.8 miles, Bachelor's Grove Cemetery - 2.36 miles, Gaelic Park - 3.05 miles

Top Crestwood Hotel Reviews

Frequently asked questions

Searching for romantic hotels in Crestwood?
Are you and your partner looking for a romantic vacation? Our guests also enjoy Crestwood for its restaurants and shopping. If you want to see some of the sights in Crestwood, you might consider checking out Hollywood Park. If you'd like to stay close to a certain attraction, you can sort by neighborhood or distance to top landmarks, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Crestwood?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Crestwood: The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 31°F. Average annual precipitation for Crestwood is 47 inches.
What is there to do in Crestwood?
There's nothing better than wandering around a new place with your sweetheart, so consider taking time to discover all there is to see and do in Crestwood. If you and your partner are interested in sampling the area's cuisine, you'll enjoy Crestwood for its restaurants. Hollywood Park is one of the local sights that might be worth a stop.
What's the best way to get to Crestwood and around town during my romantic getaway?
This information about transportation options in Crestwood might help your romantic trip go off without a hitch: If you're looking to fly to Crestwood, the closest major airport is Chicago Midway Airport (MDW), located 8.8 mi (14.2 km) from the city center. If you'd like to venture out around the area, you may want to rent a car for your trip.

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