Central Chicago Vacation Packages 2026 from $392

Central Chicago flight + hotel vacation packages

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

Hollywood Casino Aurora

$392

per person

Jul 27 - Jul 30

found 7 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a full-service spa and 9 restaurants. Valet parking is offered and the front desk is staffed around-the-clock.

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$977

per person

Aug 4 - Aug 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A business center, a picnic area, and luggage storage are also on offer.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$806

per person

Aug 21 - Aug 25

found 12 hours ago

Roundtrip flight included

Atlanta (ATL) 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.

JW Marriott Chicago

Downtown Chicago

Save 100% on your flight

$573

per person

Aug 14 - Aug 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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 business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$731

per person

Jul 27 - Jul 31

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features 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. A lobby fireplace, a communal living room, and express check-out are also on offer.

Top Central Chicago hotels deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Free Cancellation

Reserve now, pay when you stay

$154 nightly

$183 total

Jul 2 - Jul 3

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

The Chicago Hotel Collection - Magnificent Mile

166 E Superior Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$154 nightly

$183 total

Jun 28 - Jun 29

Total with taxes and fees

This boutique hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Business travelers can take advantage of the free WiFi in public areas. Self parking, express check-out, and luggage storage are also offered.

Pet friendly

Free WiFi

Hotel Riu Plaza Chicago

150 East Ontario Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$203 nightly

$242 total

Jun 30 - Jul 1

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

Freehand Chicago

19 East Ohio Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$134 nightly

$159 total

Jun 29 - Jun 30

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a coffee shop, and a snack bar/deli are also offered.

Pet friendly

Free WiFi

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Free Cancellation

Reserve now, pay when you stay

$154 nightly

$183 total

Jun 29 - Jun 30

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 free WiFi in public areas, express check-out, and valet parking. A lobby fireplace, luggage storage, and wedding services are also on offer.

Pet friendly

Free WiFi

River Hotel

75 East Wacker Drive Chicago IL

$178 nightly

$212 total

Jul 1 - Jul 2

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. Express check-in, express check-out, and dry cleaning are also on offer.

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

Soldier Field

4.5/5(1,274 reviews)

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Navy Pier

4.5/5(4,925 reviews)

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

Michigan Avenue

4.5/5(336 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.

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 $392. 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!