Northwest Side Vacations from $434
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The Latest Northwest Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Zion by IHG
Save 100% on your flight
Price was $636, price is now $434 per person
$434
per person
May 21 - May 26
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
8.8/10 Excellent! (188 reviews)
Staff was Excellent! Room was super clean!
Reviewed on Feb 20, 2026
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,344, price is now $780 per person
$780
per person
May 21 - May 26
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
Beautiful room. Property upgraded to 2-bedroom. Facilities are great with huge gym. Great stay in Chicago.
Reviewed on Mar 14, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,466, price is now $887 per person
$887
per person
May 28 - May 31
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Spacious room with great views and washer and dryer
Reviewed on Mar 17, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Save 100% on your flight
Price was $2,600, price is now $1,668 per person
$1,668
per person
May 28 - May 31
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,332 reviews)
Exceptional hotel in the best location!
Reviewed on Mar 17, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $820, price is now $559 per person
$559
per person
May 23 - May 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
The staff were extremely solicitous! The room was spotless! And the breakfast was delicious, plentiful, and included in the prove of the stay. I’ll definitely be back!
Reviewed on Mar 19, 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
2 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
$103 nightly
The price is $121 total per night from Apr 1 to Apr 2
$121 total
Apr 1 - Apr 2
Total with taxes and fees
8/10 Very Good! (9,968 reviews)
Nice room, a bit disturbed I had to pay a safety fee of$25.00 for each day of my stay.
Reviewed on Mar 20, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $183 total per night from Apr 6 to Apr 7
$183 total
Apr 6 - Apr 7
Total with taxes and fees
9.4/10 Exceptional! (3,569 reviews)
Staff was friendly, rooms were clean and breakfast was delicious
Reviewed on Mar 19, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $153 total per night from Mar 29 to Mar 30
$153 total
Mar 29 - Mar 30
Total with taxes and fees
8.6/10 Excellent! (5,749 reviews)
The location was great, near plenty of restaurants and shopping. The room was a great layout plenty of space.
Reviewed on Mar 19, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
