Deals on vacations and trips to Chicago

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Chicago flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $609, price is now $399 per person
$399
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a computer station, and dry cleaning are also offered.
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was $4,670, price is now $2,475 per person
$2,475
per person
Sep 13 - Sep 19
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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,198, price is now $750 per person
$750
per person
Oct 22 - Oct 25
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.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,140, price is now $1,383 per person
$1,383
per person
Sep 13 - Sep 19
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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,769, price is now $1,145 per person
$1,145
per person
Sep 2 - Sep 8
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, a business center, and a picnic area are also offered.

Top Chicago hotels deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
$145 nightly
The price is $172 total per night
$172 total
Aug 30 - Aug 31
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 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
$152 nightly
The price is $181 total per night
$181 total
Aug 11 - Aug 12
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
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Free Cancellation
Reserve now, pay when you stay
$169 nightly
The price is $193 total per night
$193 total
Aug 30 - Aug 31
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 business center, free WiFi in public areas, and free airport shuttle. Self parking, a coffee shop, and limo/town car service are also offered.
Free airport shuttle
Pet friendly
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$199 nightly
The price is $236 total per night
$236 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and valet parking. Self parking, a lobby fireplace, and luggage storage are also offered.
Pet friendly
Free WiFi
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$219 nightly
The price is $260 total per night
$260 total
Aug 9 - Aug 10
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. There's in-room fitness on site, and concierge services and wedding services are also offered.
Pet friendly
Free WiFi
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street Chicago IL
Free Cancellation
$224 nightly
The price is $266 total per night
$266 total
Sep 1 - Sep 2
Total with 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. Self parking, a coffee shop, and a snack bar/deli are also offered.
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.

Stay near popular Chicago attractions

An aerial view of a baseball stadium surrounded by urban buildings.
Photo by © City of Chicago
Open Photo by © City of Chicago

Wrigley Field

9.0/10 (11,704 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
See properties

Frequently asked questions

How much are vacation packages to Chicago?
Get ready to be surprised — you can vacation in Chicago for as low as $399. At Travelocity, we save you money and hassle with our excellent vacation packages. With hotels, flights and tours all in one place, why wait any longer?
How long should my Chicago vacation be?
Typically, 2 nights is what most tourists book for their Chicago trip. That's a good starting point, but there's plenty more to discover if you allow yourself a little longer.
Where can I get the best vacation package deals for Chicago?
Picking up the best package deal to Chicago is a piece of cake with Travelocity. With 400 air carriers and 1,000,000 properties all over the world, you're spoiled for choice when it comes to your hotels and flights.
Why should I purchase my Chicago vacation bundle via Travelocity?
Because you'll never roam alone if you book with us, and we offer round-the-clock support and exceptional service to boot. Add to that our Price Match Guarantee and tons of destinations to pick from. It's our job to make your daydreams a reality.
Can I save money on my Chicago car rental if I bundle it with hotels and flights?
Absolutely — combine your flight, car and hotel into a Chicago vacation package and you can save a tidy sum. With so much to see in Chicago, having your own wheels will make exploring a joy. Once you've buckled yourself in, hit the wide open road and cruise toward Six Flags Great America, a famous attraction roughly 35 mi from Chicago.
Which airport is best for Chicago?
O'Hare Intl. Airport (ORD) (16 mi away from downtown), Midway Intl. Airport (MDW) (9 mi away from central Chicago) and Lewis University Airport (LOT) (30 mi away from central Chicago) are the main hubs in Chicago.
What is there to do in Chicago?
While hopping off the tourist trail is rewarding, you really shouldn't miss the popular sights that make a place famous. Wrigley Field and Six Flags Great America are a couple of them in Chicago.
Where should I stay when visiting Chicago?
If you're after someplace comfortable to lay your head, have a look at the Congress Plaza Hotel. It's the top choice for many visitors.

Where to stay in Chicago: Best areas for travelers

Photos of local treasures

Browse Chicago vacation photos for more inspiration

A city skyline with modern skyscrapers and a river with boats and people in the foreground.
The Adler School's 2012 Commencement Ceremony at the Chicago Theatre.
A nighttime cityscape with illuminated skyscrapers and a river.
A modern building with a glass facade and a Ferris wheel in the background.
A cityscape with tall buildings partially obscured by clouds.

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