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North Side Vacations from $279
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The Latest North Side Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Hotel Felix River North/Magnificent Mile
Dec 10 - Dec 13Hotel Felix River North/Magnificent Mile + Flight
Downtown Chicago3 nights4.0 star property8.4/10 - Very good (3,165 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop$422$279found 1 day agoper traveler - Hotel Riu Plaza Chicago
Dec 10 - Dec 13Hotel Riu Plaza Chicago + Flight
Downtown Chicago3 nights4.0 star property9.4/10 - Exceptional (5,654 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop$720$449found 1 day agoper traveler - Sheraton Grand Chicago Riverwalk
Dec 10 - Dec 13Sheraton Grand Chicago Riverwalk + Flight
Downtown Chicago3 nights4.0 star property8.6/10 - Excellent (1,880 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop$599$378found 1 day agoper traveler - Eurostars Magnificent Mile
Dec 10 - Dec 13Eurostars Magnificent Mile + Flight
Downtown Chicago3 nights4.0 star property9.0/10 - Wonderful (3,989 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop$629$404found 1 day agoper traveler - Park Hyatt Chicago
Dec 10 - Dec 13Park Hyatt Chicago + Flight
Downtown Chicago3 nights5.0 star property9.6/10 - Exceptional (1,001 reviews)"Given the price point and other reviews, we came here expecting a luxury stay similar to the Waldorf Astoria, Four Seasons, and Peninsula, which are some of our favorite properties to stay at. However, everything from the service and cleanliness to the ambiance of the entrance and lobby and the amenities (other than the gym, which was excellent) is best described as an upgraded version of an average Hilton, Hyatt, or Marriott. For example, there was a hair in the bed. When we reported it, the..."Reviewed November 4, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop$1,826$1,237found 1 day agoper traveler
Discover the most popular places to visit in North Side
What to do in North Side
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travelers recommend
Chicago's Navy Pier Centennial Wheel Ticket
$24
per adult
100% of travelers recommend
North Side Hotel Deals
Hotel Zachary Chicago, a Tribute Portfolio Hotel
Hotel Zachary Chicago, a Tribute Portfolio Hotel4.0 star property
Wrigleyville, 1.4 mi from North Side
9.6 out of 10, Exceptional, (1,002 reviews)
9.6/10
Exceptional
(1,002 reviews)
$197 nightly
The price is $231
$231 total
Nov 22 - Nov 23
Total with taxes and fees
Best Western Plus Hawthorne Terrace Hotel
Best Western Plus Hawthorne Terrace Hotel3.0 star property
1.8 mi from North Side
9.0 out of 10, Wonderful, (1,002 reviews)
9.0/10
Wonderful
(1,002 reviews)
"Nice hotel"
$161 nightly
The price is $189
$189 total
Nov 22 - Nov 23
Total with taxes and fees
9.0 out of 10, Wonderful, (942 reviews)
9.0/10
Wonderful
(942 reviews)
"Our stay was wonderful. Rooms were clean, good style, nice amenities. Staff was wonderful and helped us find a great restaurant for dinner. We had an opportunity to have appetizers and drinks in the on-site restaurant and enjoyed that as well."
$248 nightly
The price is $291
$291 total
Dec 8 - Dec 9
Total with taxes and fees
Hotel Versey Chicago Lincoln Park
Hotel Versey Chicago Lincoln Park3.0 star property
1.6 mi from North Side
8.4 out of 10, Very good, (1,378 reviews)
8.4/10
Very good
(1,378 reviews)
"I was a little worried about some if the reviews I had read before planning our trip. However, we went with it and were glad we did. We would stay there again. It's a cute place located in a fun, artsy, easy going vibe location. A cute neighborhood. The building was older, however they are remodeling and we stayed in a freshly renovated room which was great. Beds were comfortable and the bathroom very nice. It was a little noisy because it sits on Diversity Pkwy. but I would somewhat expect...
$93 nightly
The price is $109
$109 total
Dec 7 - Dec 8
Total with taxes and fees
8.6 out of 10, Excellent, (1,006 reviews)
8.6/10
Excellent
(1,006 reviews)
"The room was standard clean. Hallway on 2nd carpet looks old and dirty."
$102 nightly
The price is $120
$120 total
Dec 1 - Dec 2
Total with taxes and fees
9.8 out of 10, Exceptional, (423 reviews)
9.8/10
Exceptional
(423 reviews)
$195 nightly
The price is $221
$221 total
Nov 8 - Nov 9
Total with taxes and fees
9.0 out of 10, Wonderful, (1,041 reviews)
9.0/10
Wonderful
(1,041 reviews)
$117 nightly
The price is $137
$137 total
Dec 8 - Dec 9
Total with taxes and fees
8.0 out of 10, Very good, (1,161 reviews)
8.0/10
Very good
(1,161 reviews)
"Very nice view of the lake."
$119 nightly
The price is $140
$140 total
Nov 10 - Nov 11
Total with taxes and fees
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.
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.
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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.