North Side Vacation Packages 2026 from $286

North Side flight + hotel vacation packages

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

Holiday Inn Club Vacations at Lake Geneva Resort by IHG

Save 100% on your flight

$286

per person

Feb 27 - Mar 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This smoke-free resort features a golf course, a full-service spa, and a water park. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy a meal in one of the 4 restaurants and free perks like free self parking and an area shuttle.

The French Country Inn Lake Geneva

Save 100% on your flight

$315

per person

Feb 27 - Mar 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

A private beach and a restaurant are featured at this smoke-free hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, luggage storage, and concierge services are also on offer.

Hilton Orrington / Evanston

Downtown Evanston

$332

per person

Mar 27 - Mar 30

found 14 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-in are also on offer.

Hotel Riu Plaza Chicago

Downtown Chicago

$395

per person

Mar 27 - Mar 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.

Viceroy Chicago

Downtown Chicago

Save 100% on your flight

$860

per person

Mar 9 - Mar 14

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

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. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.

Top North Side hotels deals

Hotel Lincoln

1816 N Clark Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$94 nightly

$110 total

Feb 9 - Feb 10

Total with 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, free WiFi in public areas, and valet parking. Enjoy the a rooftop terrace and conveniences like a 24-hour front desk and wedding services.

Pet friendly

Free WiFi

The Majestic Hotel

528 W Brompton Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$82 nightly

$96 total

Feb 22 - Feb 23

Total with taxes and fees

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

Free WiFi

Air conditioning

Hotel Versey Chicago Lincoln Park

644 West Diversey Parkway Chicago IL

Free Cancellation

Reserve now, pay when you stay

$73 nightly

$86 total

Feb 2 - Feb 3

Total with 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

City Suites Hotel

933 W Belmont Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$102 total

Feb 16 - Feb 17

Total with 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

Best Western Plus Hawthorne Terrace Hotel

3434 N. Broadway Avenue Chicago IL

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$140 total

Jan 26 - Jan 27

Total with taxes and fees

This hotel features a gym and a hot tub. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the sauna and free continental breakfast each morning.

Hot Tub

Breakfast included

Hotel Zachary Chicago, a Tribute Portfolio Hotel

3630 N Clark St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$178 nightly

$209 total

Jan 29 - Jan 30

Total with 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

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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 $286, 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!