Northwest Side Vacations from $203
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The Latest Northwest Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Hyatt Place Chicago/ Schaumburg
Save 100% on your flight
Price was $360, price is now $203 per person
$203
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,000 reviews)
Everything was wonderful except those small square pillows, not sure who's idea that was
Reviewed on Dec 17, 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $723, price is now $411 per person
$411
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Great location, clean room and friendly staff!
Reviewed on Dec 14, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,242, price is now $707 per person
$707
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,787 reviews)
From staff to room it was a amazing experience.
Reviewed on Dec 18, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $745, price is now $430 per person
$430
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Excellent location to stay in the heart of the city.
Reviewed on Dec 17, 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $546, price is now $322 per person
$322
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,003 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
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
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 Addison Station (Blue Line) to get around the city.
Discover the most popular places to visit in Northwest Side
Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Northwest Side
Chicago Bulls Basketball Game at United Center
$80
per adult
80% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Northwest Side Hotel Deals
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $105 total per night from Jan 5 to Jan 6
$105 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
8.8/10 Excellent! (3,516 reviews)
Nice café in the lobby. Great Staff
Reviewed on Dec 19, 2025
Silversmith Hotel Chicago Downtown
10 S Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $149 total per night from Jan 4 to Jan 5
$149 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.2/10 Wonderful! (2,136 reviews)
Clean room, amazing bathroom. Very wonderful stay. Parked in Palmer house parking garage and walked to hotel. Close to many nice restaurants and in the heart of downtown.
Reviewed on Dec 19, 2025
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $174 total per night from Dec 26 to Dec 27
$174 total
Dec 26 - Dec 27
Total with taxes and fees
8.4/10 Very Good! (2,142 reviews)
Easy check in & out. Nice clean room, pool, & hotel. Hotel is old but that lends to a bit of nostalgia as maintenance & upkeep have keep the feeling of freshness alive.
Reviewed on Dec 19, 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.
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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- Six Corners
- Visit Portage Park
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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.
