Central Chicago Vacation Packages 2026 from $286

Central Chicago 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.

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.

The Royal Sonesta Chicago Downtown

Downtown Chicago

$408

per person

Mar 20 - Mar 23

found 1 day ago

Roundtrip flight included

Boston (BOS) 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, conference space, and valet parking. WiFi in public areas, luggage storage, and concierge services are also on offer.

Trump International Hotel & Tower Chicago

Downtown Chicago

$600

per person

Mar 27 - Mar 29

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.

Top Central Chicago hotels deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$104 total

Jan 31 - Feb 1

Total with taxes and fees

This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.

Free WiFi

Restaurant

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$124 total

Feb 5 - Feb 6

Total with taxes and fees

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.

Pool

Breakfast included

Hilton Chicago

720 S Michigan Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$155 nightly

$182 total

Feb 1 - Feb 2

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

Pool

Hot Tub

Hotel Riu Plaza Chicago

150 East Ontario Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$133 nightly

$156 total

Feb 11 - Feb 12

Total with taxes and fees

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.

Breakfast included

Free WiFi

DoubleTree by Hilton Chicago - Magnificent Mile

300 E Ohio St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$85 nightly

$100 total

Feb 1 - Feb 2

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. You'll appreciate the gym, poolside bar, and concierge services.

Pool

Pet friendly

The Royal Sonesta Chicago Downtown

71 E Wacker Dr Chicago IL

Free Cancellation

Reserve now, pay when you stay

$161 nightly

$189 total

Feb 1 - Feb 2

Total with taxes and fees

Pet friendly

Free WiFi

Don't see what you're looking for?

See all available properties in Central Chicago

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

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

McCormick Place

4.5/5(1,805 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

Navy Pier

4.5/5(4,870 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Frequently asked questions

How much are vacation packages to Central Chicago?

You might be surprised — you can vacation in Central Chicago for as little as $286. At Travelocity, we save you money and stress with our excellent vacation packages. With hotels, flights and experiences all in one place, what's stopping you?

Where can I get the best vacation package deals for Central Chicago?

You'll come across a terrific range of Central Chicago package deals on Travelocity. With no less than 400 air carriers and 1,000,000 properties across the globe, piecing together the perfect escape will be easy.

Why should I purchase my Central Chicago vacation bundle via Travelocity?

Whether you're planning a weeks-long vacation or a last-minute weekend trip, we have lots of amazing destinations to choose from at a great price. And on top of that, we provide 24/7 customer support, high-quality service and a Price Match Guarantee. Save yourself time and money and book your dream vacation now.

Can I save on my Central Chicago car rental if I book it with a hotel or flight?

Most definitely — and if you also add a tour to your Central Chicago vacation package, you'll pocket even greater savings. With an affordable package from Travelocity, you can find things to do around the region that are right for you. Then, jump in your rental car and work your way through the list. Six Flags Great America is one much-loved sight to key into your GPS. It's 35 mi from Central Chicago.

What is there to do in Central Chicago?

As you're exploring Central Chicago, be sure to pay a visit to Millennium Park and Art Institute of Chicago. It's tough to get bored here!