Central Chicago Vacation Packages 2025/2026 from $336

Central Chicago flight + hotel vacation packages

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

Staybridge Suites, Lincolnshire by IHG

Half Day

Save 100% on your flight

$336

per person

Oct 22 - Oct 27

found 16 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free perks include buffet breakfast, free self parking, and an area shuttle.

The Emily Hotel

Downtown Chicago

$727

per person

Oct 31 - Nov 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Chicago Athletic Association, a Hyatt Hotel

Downtown Chicago

$857

per person

Oct 22 - Oct 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This smoke-free hotel's 2 restaurants, 3 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. There's a rooftop terrace on site, and a 24-hour front desk and a coffee shop are also provided.

Staybridge Suites Chicago O'Hare - Rosemont by IHG

O'Hare

Save 100% on your flight

$371

per person

Oct 22 - Oct 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the free buffet breakfast each morning.

Holiday Inn Chicago O'Hare – Rosemont by IHG

O'Hare

Save 100% on your flight

$349

per person

Oct 22 - Oct 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Self parking, a coffee shop, and a grocery/convenience store are also offered.

Top Central Chicago hotels deals

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

$143 nightly

$168 total

Aug 24 - Aug 25

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

The Wade

644 N Lake Shore Dr, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$151 nightly

$177 total

Sep 1 - Sep 2

Total includes taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and express check-in are also provided.

Pool

Pet friendly

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL

$161 nightly

$189 total

Sep 3 - Sep 4

Total includes 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

Palmer House a Hilton Hotel

17 E Monroe St, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$198 nightly

$229 total

Sep 2 - Sep 3

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

Pool

Spa

Hilton Garden Inn Chicago Downtown/Magnificent Mile

10 E Grand Ave, Chicago, IL

$143 nightly

$168 total

Sep 2 - Sep 3

Total includes taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. Express check-out, luggage storage, and concierge services are also on offer.

Pool

Pet friendly

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$159 nightly

$186 total

Aug 24 - Aug 25

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

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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

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

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

McCormick Place

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 $336. 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!