North Side Holidays

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North Side Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$2,619, price is now S$1,935 per person
S$1,935
per person
9 Oct - 15 Oct
found 8 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.4/10 Very Good! (4,844 reviews)
$79 for parking!!! And you are a guest at the hotel? The hotel was not bad. Breakfast was great but that parking just put a damper on the whole experience.

Reviewed on 9 Sep, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$3,515, price is now S$2,376 per person
S$2,376
per person
9 Oct - 15 Oct
found 8 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (347 reviews)
Pool area was great

Reviewed on 4 Sep, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$5,067, price is now S$3,648 per person
S$3,648
per person
9 Oct - 15 Oct
found 8 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
We picked the Trump Hotel-Chicago to celebrate our 35th Wedding Anniversary mainly for the location and the amenities. The hotel EXCEEDED our expectations in every way. (1) The staff is so warm, kind, compassionate and extremely professional in such a friendly down-to-earth way. (2) The property itself is immaculate. (3) The amenities: Terrace 16- the view will take your breath away! The food/cocktails were fabulous as was the service. (3) Pablo - Director of Rooms, Curtis -Concierge were off the charts fabulous. I wish I could remember all the staff names that went out of their way to make our weekend so special. I cannot wait to stay here again. As another reviewer said: put any political opinions aside and treat yourself to a stay here. YOU WILL LOVE IT. (There is no political aura here...only a fantastic team that wants you to enjoy your stay and they go out of their way to make sure you do).

Reviewed on 8 Sep, 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$2,901, price is now S$2,105 per person
S$2,105
per person
9 Oct - 15 Oct
found 8 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.2/10 Very Good! (2,115 reviews)
Overall enjoyed my stay at the property. Only thing I had an issue with was connecting to the streaming and it staying connected. After an hour, the TV would disconnect and it was a process to get it back up. Other than that, loved everything else

Reviewed on 8 Sep, 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$2,994, price is now S$2,197 per person
S$2,197
per person
9 Oct - 15 Oct
found 8 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
Perfect place in the Loop. Customer service was perfect on all fronts.

Reviewed on 9 Sep, 2025

Where to stay in North Side

Find the best North Side areas and neighborhoods for the activities you enjoy most. Learn more about North Side
Chicago which includes a city and modern architecture

Lincoln Park

5 out of top 10 points of interest in this area
5/5(5 area reviews)

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Find hotels in Lincoln Park

Top hotels in North Side

The Majestic Hotel

The Majestic Hotel

3 out of 5
528 W Brompton Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$261 per night from 7 Oct to 8 Oct
S$261
7 Oct - 8 Oct
includes taxes & fees
The Majestic Hotel
Hotel Lincoln

Hotel Lincoln

4 out of 5
1816 N Clark Street, Chicago, IL
The price is S$224 per night from 23 Sept to 24 Sept
S$224
23 Sept - 24 Sept
includes taxes & fees
Hotel Lincoln
The Willows Hotel

The Willows Hotel

3 out of 5
555 W Surf St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$242 per night from 29 Sept to 30 Sept
S$242
29 Sept - 30 Sept
includes taxes & fees
The Willows Hotel
See all 536 properties in North Side
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.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
Lincoln Park Zoo which includes zoo animals and land animals as well as a couple

Lincoln Park Zoo

This small zoo right in the heart of Chicago, Lincoln Park is an ideal family destination, popular with small children eager to see the many different animals.

Lincoln Park Zoo
Lincoln Park Conservatory featuring interior views, flowers and a garden

Lincoln Park Conservatory

This glass structure full of exotic plants is the perfect place to spend a quiet afternoon.

Lincoln Park Conservatory

What to do in North Side

River tour boat in Chicago

Architecture River Tour

S$63
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$58
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

S$32
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in North Side

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.