Near North Side Vacations from $420

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Your Near North Side Vacation

Your next escape beckons with a vacation package to Near North Side. Entertainment, relaxation and nonstop great times — you're sure to find it in this neighborhood. When it's time to get out and explore, you'll find a lot of popular attractions nearby including Millennium Park, Willis Tower and Art Institute of Chicago. Visit one, two or all during your trip to Near North Side. Stop dreaming and start doing. When you're ready to lock in your vacation to Near North Side, Expedia is here to help.

The Latest Near North Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Deerfield
Sable at Navy Pier Chicago, Curio Collection by Hilton
Hotel Riu Plaza Chicago
Chicago Athletic Association, a Hyatt Hotel
Hotel Felix River North/Magnificent Mile

Where to stay in Near North Side

Find the best Near North Side areas and neighborhoods for the activities you enjoy most. Learn more about Near North Side

Near North Side Hotel Deals

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $177 total per night from Sep 1 to Sep 2
$177 total
Sep 1 - Sep 2
Total with taxes and fees
8.2/10 Very Good! (1,220 reviews)
Room clean and modern
"It was great and I appreciated the friendly staff and the cleanliness of my room. It was also very modern and just felt up to date."

Reviewed on Aug 25, 2025

The Wade
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $179 total per night from Sep 3 to Sep 4
$179 total
Sep 3 - Sep 4
Total with taxes and fees
8.4/10 Very Good! (4,765 reviews)
"Everyone was very helpful and polite. The room was clean and spacious. My kids loved the breakfast and snacks at night."

Reviewed on Aug 23, 2025

Embassy Suites by Hilton Chicago Downtown River North
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $168 total per night from Sep 2 to Sep 3
$168 total
Sep 2 - Sep 3
Total with taxes and fees
8.4/10 Very Good! (3,763 reviews)
"Nice hotel. Convenient to restaurants."

Reviewed on Aug 25, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
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.

Discover the most popular places to visit in Near North Side

Things to do

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.