North Side Vacation Packages 2025 from $487

North Side flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

La Banque Hotel

Save 100% on your flight

per person

Jul 16 - Jul 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

Jul 28 - Jul 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Harrah's Joliet Casino & Hotel

Save 100% on your flight

per person

Aug 15 - Aug 17

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (CHI)

This hotel features 3 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, express check-out, and luggage storage are also on offer.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

per person

Jul 28 - Jul 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

A full-service spa and A 24-hour gym are featured at this smoke-free aparthotel. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and perks like free WiFi.

Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Save 100% on your flight

per person

Jul 28 - Jul 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.

Top North Side hotels deals

Chicago Getaway Hostel

616 W Arlington Pl, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$65 nightly

$77 total

Jun 30 - Jul 1

Total includes taxes and fees

This hostel features a terrace, laundry facilities, and self parking. Enjoy the free continental breakfast each morning. A business center, a garden, and a library are also on offer.

Breakfast included

Air conditioning

Hotel Lincoln

1816 N Clark Street, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$147 nightly

$173 total

Jul 7 - Jul 8

Total includes taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, laundry service, and valet parking. Enjoy the a rooftop terrace and conveniences like a 24-hour front desk and wedding services.

Pet friendly

Restaurant

The Majestic Hotel

528 W Brompton Ave, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$141 nightly

$166 total

Jul 9 - Jul 10

Total includes taxes and fees

A gym is featured at this hotel, along with free WiFi in public areas and a fireplace in the lobby. Dry cleaning, luggage storage, and laundry facilities are also on offer.

Free WiFi

Air conditioning

City Suites Hotel

933 W Belmont Ave, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$168 total

Jul 7 - Jul 8

Total includes taxes and fees

A gym, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A lobby fireplace, express check-out, and luggage storage are also on offer.

Free WiFi

Air conditioning

Hotel Versey Chicago Lincoln Park

644 West Diversey Parkway, Corner Diversey/Clark/Broadway, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$141 nightly

$165 total

Jul 7 - Jul 8

Total includes taxes and fees

This hotel features free WiFi in public areas, concierge services, and self parking. There's luggage storage and multilingual staff can provide around-the-clock assistance.

Pet friendly

Free WiFi

Hotel Zachary Chicago, a Tribute Portfolio Hotel

3630 N Clark St, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$284 nightly

$334 total

Jun 23 - Jun 24

Total includes taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a garden, and a lobby fireplace are also offered.

Pet friendly

Free WiFi

Don't see what you're looking for?

See all available properties in North Side

View all properties

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

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Lincoln Park Zoo

4.5/5(793 reviews)

This small zoo in the center of Chicago is perfect for small children and parents looking for a quiet, leisurely stroll — and some impressive animals!

Chicago History Museum

4.5/5(23 reviews)

Take a stroll through time, with historical artifacts that explore the city’s rich and colorful history.

Frequently asked questions

How much are vacation packages to North Side?

With vacation packages being sold for only $487, you won’t need to blow out the credit card for your visit to North Side. Travelocity can help. Combine experiences, flights and hotels into a package and land exciting discounts. The more you book, the more you save.

Where can I get the best vacation package deals for North Side?

Travelocity is the place to go to score an awesome North Side package deal. Select from 400 air carriers and 1,000,000 properties worldwide and craft a vacation package that fits your style. With almost endless choice, you’ll have plenty of inspiration for your next big adventure.

Why should I book my North Side vacation bundle with Travelocity?

Because we believe in crafting special vacation experiences. From flights and hotels to car rentals and activities, our packages make traveling a breeze. Our customer support is available 24/7 to ensure you’re being well taken care of. We also have a Price Match Guarantee, so you can book your getaway knowing you’ve scored the best deal possible. If you find a lower price, we’ll match it!

Can I save on my North Side car rental if I combine it with hotels and flights?

Most definitely — and booking one of our North Side vacation packages is the simplest way to go about this. Bundle any combination of a hotel, flight, car and experience and score awesome discounts. The more you book, the more you save. There are so many exciting sights around North Side to put on your to-do list, including Six Flags Great America (35 mi from North Side). Nothing beats exploring thrilling places like this with the freedom of your own car rental.

What is there to do in North Side?

As you’re strolling through North Side, don’t forget to pay a visit to Wrigley Field and Lincoln Park Zoo. You won’t be short of things to do!