Book Exclusive Chicago Vacation Packages

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Chicago flight + hotel packages

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Theatre District
Price was CA $1,245, price is now CA $926 per person
per person
Nov 17 - Nov 21
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 3 bars/lounges. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Millennium Park and Navy Pier are located nearby. Discover genuine guest reviews for Chicago Athletic Association, a Hyatt Hotel, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
The LaSalle Chicago, Autograph Collection

The LaSalle Chicago, Autograph Collection

4 out of 5
Theatre District
Save 100% on your flightPrice was CA $1,408, price is now CA $1,095 per person
per person
Nov 8 - Nov 12
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, a restaurant, and a full-service spa. Popular attractions Millennium Park and Navy Pier are located nearby. Discover genuine guest reviews for The LaSalle Chicago, Autograph Collection, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
The Langham, Chicago

The Langham, Chicago

5 out of 5
River North
Price was CA $2,032, price is now CA $1,581 per person
per person
Dec 9 - Dec 13
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Millennium Park and Navy Pier are located nearby. Discover genuine guest reviews for The Langham, Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
River North
Price was CA $1,397, price is now CA $1,095 per person
per person
Nov 17 - Nov 21
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Millennium Park and Navy Pier are located nearby. Discover genuine guest reviews for The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
The Loop
Price was CA $1,106, price is now CA $872 per person
per person
Dec 9 - Dec 13
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Navy Pier are located nearby. Discover genuine guest reviews for Hyatt Regency Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.

Top Chicago hotels deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL, 60605
Free cancellation
Reserve now, pay when you stay
The price is CA $185 per night
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Navy Pier are located nearby. Discover genuine guest reviews for Congress Plaza Hotel, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Free WiFi
Air conditioning
The Whitehall Hotel

The Whitehall Hotel

4 out of 5
105 E Delaware Pl, Chicago, IL, 60611
Free cancellation
Reserve now, pay when you stay
The price is CA $161 per night
Stay at this 4-star boutique hotel in Chicago. Enjoy free WiFi, breakfast, and a fitness center. Our guests praise the clean rooms and the overall value in our reviews. Popular attractions Millennium Park and Navy Pier are located nearby. Discover genuine guest reviews for The Whitehall Hotel, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Free WiFi
Pet-friendly
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL, 60611
Free cancellation
Reserve now, pay when you stay
The price is CA $157 per night
Stay at this 4-star family-friendly hotel in Chicago. Enjoy WiFi, a 24-hour fitness center, and valet parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Navy Pier are located nearby. Discover genuine guest reviews for Warwick Allerton - Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Pet-friendly
Air conditioning
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street, Chicago, IL, 60603
Free cancellation
Reserve now, pay when you stay
The price is CA $216 per night
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Navy Pier are located nearby. Discover genuine guest reviews for Club Quarters Hotel, Central Loop, Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Free WiFi
Pet-friendly
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL, 60611
Free cancellation
Reserve now, pay when you stay
The price is CA $211 per night
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Navy Pier and Millennium Park are located nearby. Discover genuine guest reviews for Hilton Chicago/Magnificent Mile Suites, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Pool
Free WiFi
Hilton Garden Inn Chicago Downtown Riverwalk

Hilton Garden Inn Chicago Downtown Riverwalk

3 out of 5
66 East Wacker Place, Chicago, IL, 60601
Free cancellation
Reserve now, pay when you stay
The price is CA $228 per night
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Navy Pier are located nearby. Discover genuine guest reviews for Hilton Garden Inn Chicago Downtown Riverwalk, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Free WiFi
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.

Chicago Vacations

If you were away the day your geography teacher told your class where Chicago is situated, you don't have to stress. With some help from us, you'll be able to find it easily!

Chicago sits 80 miles (129 kilometers) south of Milwaukee, a significant city.

At last count, the population of this area of Illinois was 2,700,000.

Places to visit in Chicago

With a multitude of famous sights in Chicago, it'd be wise to take a pair of comfortable shoes. Number one on your bucket list should be an outing to the Art Institute of Chicago and Willis Tower. After that, you might need to crank up the pace a bit as you shouldn't go home without swinging by the McCormick Place and the University of Illinois Chicago.

Experience the true essence of this bustling metropolis by exploring attractions like Navy Pier and the Lincoln Park Zoo. If you want more options, Lincoln Park and the Chicago Cultural Center are well worth visiting too.

Millennium Park is a lush haven that's easily accessible from the main central area. After a busy morning of exploring, wind down in one of its shady spots. Like some more ideas? Crane your neck back and look up — way up! John Hancock Center is among the most eye-catching structures in the local skyline and one that's tough to miss. And there's more. Skydeck Ledge offers awe-inspiring vistas as well as some unmissable photo opportunities.

Where do you fly into for Chicago?

While you're planning your Chicago getaway, keep in mind that the closest airport, Midway International Airport (MDW), is approximately 9 miles (14 kilometers) to the southwest of the city center. Book your airfares, fill up your luggage and get set for some exciting new adventures!

Frequently asked questions

How much are vacation packages to Chicago?
Treat yourself to a fulfilling travel experience in Chicago with a vacation package starting from as low as CA $872. Locking in your flights, hotels and tours through Travelocity is simple. On top of that, our package deals will leave you with more money in your pocket for fun times.
How long should my Chicago vacation be?
Many visitors like to spend about 2 nights in Chicago. But that’s not set in stone. Whether you opt to stay for a few days or a few weeks, you’ll love discovering all the incredible things that this place has to offer.
Where can I get the best vacation package deals for Chicago?
There are awesome Chicago package deals to score with Travelocity. Did you know we partner with 400 airlines and 665,000 properties around the globe? Keep this in mind the next time you’re ready to cross another destination off the old bucket list.
Why should I book my Chicago vacation bundle via Travelocity?
With our Price Match Guarantee, we’ll match any cheaper price you’re able to find. Add on our 24/7 support and top-shelf service and your perfect vacation is closer than ever before.
Will I save money on my Chicago car rental if I bundle it with hotels and flights?
Combining your flight, hotel and car into a Chicago vacation package is an easy way to score better prices. Plus, having your own wheels gives you absolute freedom to find your way to all those big sights you’d like to explore. Located 60 kilometersfrom Chicago, Six Flags Great America is one attraction that should be on your to-do list. Put together a driving playlist and make a day trip of it.
What is the best time of year to go to Chicago?
is high season here, while are the quietest months. If your budget is your top consideration, try to avoid visiting during as it’s generally the most expensive time. The least expensive month to visit is .
Which airport is best for Chicago?
There’s a very good chance you’ll be arriving at Chicago, IL (ORD-O’Hare Intl.), situated 26 kilometersnorthwest of inner Chicago. Chicago, IL (MDW-Midway Intl.) (14 kilometersaway from central Chicago) and Romeoville, IL (LOT-Lewis University) (50 kilometersaway from central Chicago) are other options.
What is there to do in Chicago?
Chicago is teeming with sights to discover, such as Wrigley Field and Millennium Park. These two fantastic attractions are on most visitors’ must-see lists.
Where should I stay when visiting Chicago?
You’ll hear travelers recommending Downtown Chicago. If you choose to start your Chicago adventures here, have a look at the Congress Plaza Hotel (3.0 stars) and the Hyatt Regency Chicago (4.0 stars). Another awesome neighborhood to base yourself in is Magnificent Mile. Favorite hotels here include the Warwick Allerton - Chicago (4.0 stars) and The Westin Michigan Avenue Chicago (4.5 stars).
Can I go on vacation to Chicago at this time?
Find out all the info that’s important relating to travel restrictions and quarantine policies ahead of your journey to Chicago. Our Covid-19 Travel Advisor is full of useful advice to help make your trip smooth and hassle-free.