Central Chicago Vacation Packages 2025 from $340

Central Chicago flight + hotel vacation packages

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

Hilton Garden Inn Hoffman Estates

Save 100% on your flight

per person

Jul 3 - Jul 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and free WiFi. A coffee shop, a grocery/convenience store, and a lobby fireplace are also on offer.

The French Country Inn Lake Geneva

Save 100% on your flight

per person

Jul 21 - Jul 24

found 5 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

A private beach and a restaurant are featured at this smoke-free hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A picnic area, luggage storage, and concierge services are also on offer.

Chicago River Side Suites

Downtown Chicago

Save 100% on your flight

per person

Jul 1 - Jul 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel includes a communal living room and a virtual front desk.

Level Chicago - River North

Downtown Chicago

Save 100% on your flight

per person

Aug 2 - Aug 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, laundry facilities, and concierge services are also on offer.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

Jul 10 - Jul 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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

$161 nightly

$189 total

Jun 29 - Jun 30

Total includes 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

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago, IL

$163 nightly

$192 total

Jun 30 - Jul 1

Total includes 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

Warwick Allerton - Chicago

701 North Michigan Avenue, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$145 nightly

$171 total

Jun 30 - Jul 1

Total includes taxes and fees

This hotel features a 24-hour gym and a bar/lounge. Families will appreciate the onsite laundry facilities and babysitting. Traveling on business? Take advantage of the 24-hour business center, express check-out, and valet parking.

Air conditioning

Gym

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$157 nightly

$185 total

Jun 3 - Jun 4

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 free WiFi in public areas, express check-in, and valet parking. A coffee shop, a snack bar/deli, and a lobby fireplace are also on offer.

Pet friendly

Free WiFi

citizenM Chicago Downtown

80 East Wacker Place, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$156 nightly

$184 total

Jun 29 - Jun 30

Total includes taxes and fees

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

Free WiFi

Restaurant

The Westin Michigan Avenue Chicago

909 North Michigan Ave, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$198 total

Jun 30 - Jul 1

Total includes 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 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.

Spa

Pet friendly

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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

Navy Pier

4.5/5(4,870 reviews)

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

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.

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 $340. 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!