Deals on vacations and trips to Central Chicago

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Central Chicago flight + hotel vacation packages

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Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $881, price is now $548 per person
$548
per person
Nov 5 - Nov 8
found 1 day 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.
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,959, price is now $1,137 per person
$1,137
per person
Nov 5 - Nov 8
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 smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and laundry facilities.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,301, price is now $787 per person
$787
per person
Nov 13 - Nov 16
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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,088, price is now $660 per person
$660
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, a business center, and a picnic area are also offered.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,159, price is now $715 per person
$715
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

Top Central Chicago hotels deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$112 nightly
The price is $133 total per night
$133 total
Sep 8 - Sep 9
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.
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $144 total per night
$144 total
Sep 8 - Sep 9
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
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Get rates
A gym, self parking, and a virtual front desk are featured at this aparthotel. WiFi in public areas is free. A convenience store and luggage storage are also provided.
Kitchen
Washer
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
$158 nightly
The price is $188 total per night
$188 total
Sep 7 - Sep 8
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.
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
$194 nightly
The price is $230 total per night
$230 total
Sep 10 - Sep 11
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.
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
$228 nightly
The price is $271 total per night
$271 total
Sep 7 - Sep 8
Total with taxes and fees
This smoke-free hotel's 4 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A terrace, a snack bar/deli, and express check-in are also on offer.
Free WiFi
Restaurant
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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.

Stay near popular Central Chicago attractions

A Ferris wheel and a carousel at a fairground.

Navy Pier

9.0/10 (24,140 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
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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 $548. 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!

Photos of local treasures

Browse Central Chicago vacation photos for more inspiration

A city skyline at dusk with illuminated buildings reflecting on the water.
A person overlooking a cityscape from a high vantage point.
The Chicago Theatre with illuminated marquee and a wet street reflecting lights.
A white lighthouse with a red roof on a rocky outcrop in the ocean.
A historic stone building with intricate architecture and a modern skyscraper in the background.

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