Northwest Side Vacations from $502
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The Latest Northwest Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,053, price is now $670 per person
$670
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,714 reviews)
Very clean, great location and friendly staff. Great breakfast!
Reviewed on Jul 22, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,037, price is now $697 per person
$697
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,603 reviews)
Hotel was nice and close to the amenities of the pier. Only downside was most attractions are in the city which makes this location not as ideal.
Reviewed on Jul 22, 2026
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View all tripsWhere 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
4 out of top 10 points of interest in this area
Irving Park is well-liked for its restaurants and live music. If you're hoping to get in some sightseeing, Milwaukee Avenue and Avondale Music Hall are top spots, and you can jump on the metro at Irving Park Station (Blue Line) or Addison Station (Blue Line) to get around.
Stay near popular Northwest Side attractions
What to do in Northwest Side
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Northwest Side Hotel Deals
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
$189 nightly
The price is $215 total per night from Aug 6 to Aug 7
$215 total
Aug 6 - Aug 7
Total with taxes and fees
8.8/10 Excellent! (2,878 reviews)
"My Fourth of July weekend stay was nothing short of extraordinary. From the moment I arrived, I was welcomed with an incredible level of hospitality, professionalism, and attention to detail that immediately set the tone for an unforgettable experience. Every aspect of my stay exceeded my expectations, ..."
Reviewed on Jul 22, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$181 nightly
The price is $215 total per night from Aug 9 to Aug 10
$215 total
Aug 9 - Aug 10
Total with taxes and fees
8.2/10 Very Good! (1,805 reviews)
"Still waiting to receive the $150 deposit they charged upon arrival - it's been well over a week and has yet to come back to my account."
Reviewed on Jul 22, 2026
The Wade
644 N Lake Shore Dr Chicago IL
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $177 total per night from Aug 9 to Aug 10
$177 total
Aug 9 - Aug 10
Total with taxes and fees
8.6/10 Excellent! (1,933 reviews)
"The king room with a view of the lake was quite spacious and perfect for our needs. The only downside was parking was quite expensive at $86/night."
Reviewed on Jul 22, 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 Northwest Side Vacation Packages
Northwest Side Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
