Northwest Side Vacations from $571
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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 $1,093, price is now $691 per person
$691
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
Included breakfast was great. Very responsive. Our shower drain was clogged; they fixed it the evening we reported it.
Reviewed on Jun 29, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,246, price is now $821 per person
$821
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Clean room and staff was great.
Reviewed on Jun 28, 2026
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,120, price is now $746 per person
$746
per person
Sep 3 - Sep 6
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,134 reviews)
Hotel is phenomenal and location is beyond.
Reviewed on Jun 26, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,365, price is now $925 per person
$925
per person
Aug 6 - Aug 9
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026
Don't see what you're looking for?
See all available trips from Columbus to Northwest Side
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
5 out of top 10 points of interest in this area
4/5(1 area review)
Irving Park is well-liked for its restaurants and live music. If you're hoping to get in some sightseeing, Milwaukee Avenue and Irish American Heritage Center 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
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $157 total per night from Jun 30 to Jul 1
$157 total
Jun 30 - Jul 1
Total with taxes and fees
8/10 Very Good! (10,166 reviews)
"Charm"
Reviewed on Jun 29, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$178 nightly
The price is $212 total per night from Jul 7 to Jul 8
$212 total
Jul 7 - Jul 8
Total with taxes and fees
9.2/10 Wonderful! (1,833 reviews)
"Staff was extremely friendly and helpful! Very clean and inviting environment!"
Reviewed on Jun 29, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $175 total per night from Jul 6 to Jul 7
$175 total
Jul 6 - Jul 7
Total with taxes and fees
9/10 Wonderful! (4,480 reviews)
"I liked how they answered all my questions and was super nice to our out of town group."
Reviewed on Jun 29, 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.
