Northwest Side Vacations from $289
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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 $1,163, price is now $652 per person
$652
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Great location right off of Michigan Ave. They have a very good breakfast, that included almost everything you could want. It was very popular and packed with people. One negative, it felt like it was a cafeteria and not a relaxing place to sit down, relax and enjoy.
Reviewed on Mar 9, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was $1,462, price is now $892 per person
$892
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,613 reviews)
Every thing was amazing the staff was friendly and helpful shops and everything was close by I loved it thank you again
Reviewed on Mar 9, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $1,921, price is now $1,215 per person
$1,215
per person
Jun 1 - Jun 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,070 reviews)
Very nice & clean hotel and near the Bean and shops are walkable.
Reviewed on Mar 3, 2026
Hilton Chicago O'Hare Airport
O'Hare
Price was $856, price is now $544 per person
$544
per person
Jun 4 - Jun 8
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (2,217 reviews)
Very convenient loved the restaurant. Food and staff was amazing.
Reviewed on Mar 8, 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
Skydeck - Willis Tower Admission
$44
per adult
98% of travellers recommend
Chicago Bulls Basketball Game at United Center
$61
per adult
80% of travellers recommend
Northwest Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $118 total per night from Apr 1 to Apr 2
$118 total
Apr 1 - Apr 2
Total with taxes and fees
8/10 Very Good! (9,938 reviews)
Good: Clean; friendly staff. Bad: hot water stopped working at some point; safe was not working; lightbulb kept flickering; ice machine was broken on the 10th floor
Reviewed on Mar 9, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$162 nightly
The price is $190 total per night from Mar 18 to Mar 19
$190 total
Mar 18 - Mar 19
Total with taxes and fees
9.4/10 Exceptional! (3,498 reviews)
Great location right off of Michigan Ave. They have a very good breakfast, that included almost everything you could want. It was very popular and packed with people. One negative, it felt like it was a cafeteria and not a relaxing place to sit down, relax and enjoy.
Reviewed on Mar 9, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
$122 nightly
The price is $143 total per night from Mar 22 to Mar 23
$143 total
Mar 22 - Mar 23
Total with taxes and fees
8.6/10 Excellent! (5,745 reviews)
Love the complimentary drinks !
Reviewed on Mar 10, 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
- Hanson Park
- Visit Belmont Cragin
- Chicago Vacations
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- Visit Irving Park
- Visit Hermosa
- Visit Mayfair
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- Milwaukee Avenue
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- Visit Jefferson Park
- Logan Square Farmers Market
- Visit Albany 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.
