Central Chicago Vacation Packages 2026 from $295

Central Chicago flight + hotel vacation packages

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

theWit Chicago, a Hilton Hotel

Downtown Chicago

Save 100% on your flight

$295

per person

Mar 20 - Mar 23

found 14 hours ago

Roundtrip flight included

Austin (AUS) to Chicago (ORD)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Limo/town car service, WiFi in public areas, and express check-out are also on offer.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$297

per person

Mar 9 - Mar 12

found 11 hours ago

Roundtrip flight included

Austin (AUS) to Chicago (ORD)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$342

per person

Mar 20 - Mar 23

found 14 hours ago

Roundtrip flight included

Austin (AUS) 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.

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$386

per person

Mar 20 - Mar 23

found 14 hours ago

Roundtrip flight included

Austin (AUS) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.

4BR Corporate Suite Central and Modern

Near North Side

Save 100% on your flight

$1,448

per person

Mar 12 - Mar 16

found 7 hours ago

Roundtrip flight included

Austin (AUS) to Chicago (ORD)

A 24-hour gym, self parking, and a virtual front desk are featured at this apartment. WiFi in public areas is free.

Top Central Chicago hotels deals

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$105 total

Jan 14 - Jan 15

Total with taxes and fees

A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.

Pet friendly

Free WiFi

Hilton Chicago

720 S Michigan Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$164 nightly

$192 total

Jan 14 - Jan 15

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

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$168 nightly

$192 total

Jan 14 - Jan 15

Total with taxes and fees

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 business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and limo/town car service.

Pool

Spa

Club Quarters Hotel Wacker at Michigan, Chicago

75 E Wacker Dr Chicago IL

$88 nightly

$103 total

Jan 30 - Jan 31

Total with taxes and fees

A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A snack bar/deli, express check-in, and express check-out are also on offer.

Pet friendly

Free WiFi

Sable at Navy Pier Chicago, Curio Collection by Hilton

900 E Grand Chicago IL

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$153 total

Jan 20 - Jan 21

Total with taxes and fees

This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a coffee shop, and a terrace 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

$93 nightly

$110 total

Jan 21 - Jan 22

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

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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

Magnificent Mile - River North showing night scenes, a city and signage

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.

Navy Pier

4.5/5(4,870 reviews)

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

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.

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 $295. 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!