Northwest Side Vacations from $508
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The Latest Northwest Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $842, price is now $557 per person
$557
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,797 reviews)
I would definitely stay here again! Convenient location, walkable from most things. Staff were amazing and so helpful. Basic rooms, decent size. Very clean, great bar.
Reviewed on Jul 1, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,376, price is now $926 per person
$926
per person
Aug 6 - Aug 9
found 1 day 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
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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
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.
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
$149 nightly
The price is $177 total per night from Jul 2 to Jul 3
$177 total
Jul 2 - Jul 3
Total with taxes and fees
8/10 Very Good! (10,185 reviews)
"This place was really horrible! The shower was cold as hell and the front desk didn't do anything to help. The room was not wiped down properly and I left first thing on the A.M. when I told the front desk about my stay, they did nothing to fix the issue or reimburse me a portion of my money. I came ..."
Reviewed on Jul 1, 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 6 to Jul 7
$212 total
Jul 6 - Jul 7
Total with taxes and fees
9.2/10 Wonderful! (1,825 reviews)
"My husband and I and my daughter in law stayed at the omni because my son was having surgery at northwestern hospital. Is surgery was at 7:30 am and lasted almost 8 hours check in was not until 4, but they really understood our situation they were able to get into our room at noon. So we can rest. ..."
Reviewed on Jul 1, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$158 nightly
The price is $188 total per night from Jul 9 to Jul 10
$188 total
Jul 9 - Jul 10
Total with taxes and fees
9/10 Wonderful! (4,474 reviews)
"Friendly staff. Our room was comfortable and clean."
Reviewed on Jun 30, 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.
