Northwest Side Vacations
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Where to stay in Northwest Side
Find the best Northwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Northwest Side
Irving Park
2 out of top 10 points of interest in this area
4/5(1 area review)
Appreciated for its restaurants and live music, you might consider exploring Irving Park. Check out the variety of things to see and do like Milwaukee Avenue, and jump on the metro at Irving Park Station (Blue Line) or Montrose Station (Blue Line) to get around the city.
Find the Best Northwest Side Vacation Packages
Northwest Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩205,204 per night from Sep 22 to Sep 23
₩205,204
₩240,888 total
Sep 22 - Sep 23
includes taxes & fees
7.8/10 Good! (9,216 reviews)
"Could use more front desk staff. Quite a line formed behind me"
Reviewed on Sep 18, 2025
Freehand Chicago
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩170,411 per night from Oct 1 to Oct 2
₩170,411
₩265,227 total
Oct 1 - Oct 2
includes taxes & fees
7.8/10 Good! (2,329 reviews)
"It’s not bad, but it is a little more run down that other Freehands"
Reviewed on Sep 16, 2025
citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩217,097 per night from Sep 22 to Sep 23
₩217,097
₩254,850 total
Sep 22 - Sep 23
includes taxes & fees
9.2/10 Wonderful! (3,813 reviews)
"Please try to restock luggage tag bands"
Reviewed on Sep 17, 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 Northwest Side
Navy Pier
4.5/5(4,870 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Millennium Park
4.5/5(7,198 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Grant Park
4.5/5(3,318 reviews)
Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.
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