North Side Vacation Packages 2025/2026 from $435

North Side flight + hotel vacation packages

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

Baymont by Wyndham Gurnee

Save 100% on your flight

per person

Sep 27 - Oct 4

found 1 day ago

Roundtrip flight included

San Diego (SAN) to Chicago (ORD)

This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

per person

Oct 9 - Oct 12

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.

Homewood Suites by Hilton Chicago-Downtown

Downtown Chicago

Save 100% on your flight

per person

Oct 26 - Nov 2

found 8 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features an indoor pool and a gym. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. Valet parking, a lobby fireplace, and express check-out are also offered.

Holiday Inn Chicago North Shore by IHG

Save 100% on your flight

per person

Oct 9 - Oct 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Enjoy the gym and perks like free self parking.

Park Hyatt Chicago

Downtown Chicago

Save 100% on your flight

per person

Oct 4 - Oct 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.

Top North Side hotels deals

The Majestic Hotel

528 W Brompton Ave, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$167 nightly

$196 total

Sep 16 - Sep 17

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

Hotel Lincoln

1816 N Clark Street, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$141 nightly

$166 total

Sep 14 - Sep 15

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

Chicago Getaway Hostel

616 W Arlington Pl, Chicago, IL

Get rates

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

City Suites Hotel

933 W Belmont Ave, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$198 total

Aug 24 - Aug 25

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

The Willows Hotel

555 W Surf St, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$167 nightly

$196 total

Sep 15 - Sep 16

Total includes taxes and fees

Free WiFi in public areas, a fireplace in the lobby, and luggage storage are available at this hotel. A safe deposit box is provided and the front desk is staffed around-the-clock.

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

$118 nightly

$139 total

Aug 25 - Aug 26

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

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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

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

Lincoln Park Zoo

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

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 $435, 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!