Northwest Side Vacations from $311
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The Latest Northwest Side vacation packages
Price found within the past 48 hours. Click for updated prices.
La Banque Hotel
Save 100% on your flight
Price was $508, price is now $311 per person
$311
per person
May 4 - May 7
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.
Reviewed on Jan 26, 2026
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination
Save 100% on your flight
Price was $636, price is now $409 per person
$409
per person
May 1 - May 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (999 reviews)
Elevator was broken all three days we were there, so line could back up to get in. Food at the diner was ok but not great, with very little to eat out in the area, we ended up door dashing mostly. Steakhouse was really good, but very expensive $98 ribeye with no sides included expensive, but nice for a date night. Beds were not comfortable and pillows even worse, but will say room was clean.
Reviewed on Feb 17, 2026
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $820, price is now $531 per person
$531
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Everything was great
Reviewed on Feb 18, 2026
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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
3 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.
Discover the most popular places to visit in Northwest Side
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
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
$166
per adult
80% of travellers recommend
Chicago River: 1.5-Hour Guided Architecture Cruise
$44
per adult
98% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Northwest Side Hotel Deals
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $144 total per night from Mar 4 to Mar 5
$144 total
Mar 4 - Mar 5
Total with taxes and fees
9.2/10 Wonderful! (3,377 reviews)
Everyone are helpful breakfast is amazing
Reviewed on Feb 20, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $109 total per night from Feb 22 to Feb 23
$109 total
Feb 22 - Feb 23
Total with taxes and fees
8/10 Very Good! (9,913 reviews)
Everything was clean and neat.
Reviewed on Feb 19, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $125 total per night from Mar 3 to Mar 4
$125 total
Mar 3 - Mar 4
Total with taxes and fees
8.4/10 Very Good! (5,676 reviews)
overall was great, would definitely recommend! breakfast was great, the evening reception was a sweet bonus (they lay out little snacks every evening). pool was decent, fitness center was good not great. lobby and eating area are great, location downtown can't be beat!
Reviewed on Feb 20, 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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- Six Corners
- Visit Portage Park
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- Milwaukee Avenue
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- Visit Jefferson Park
- Logan Square Farmers Market
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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.
