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Chicago flight + hotel packages

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was CA $2,084, price is now CA $1,530 per person
per person
Aug. 7 - Aug. 10
Roundtrip non-stop flight included
Montreal (YUL) 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 breakfast and the helpful staff in our reviews. Popular attractions Millennium Park and Grant Park are located nearby. Discover genuine guest reviews for The Langham, Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,922, price is now CA $1,436 per person
per person
Aug. 7 - Aug. 10
Roundtrip non-stop flight included
Montreal (YUL) 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 clean rooms in our reviews. Popular attractions Millennium Park and Grant Park are located nearby. Discover genuine guest reviews for Trump International Hotel & Tower Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Price was CA $1,592, price is now CA $1,217 per person
per person
Aug. 26 - Sep. 1
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Grant Park and Soldier Field are located nearby. Discover genuine guest reviews for Homewood Suites by Hilton Chicago Downtown South Loop, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
Price was CA $1,194, price is now CA $920 per person
per person
Aug. 7 - Aug. 10
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast, and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Millennium Park and Grant Park are located nearby. Discover genuine guest reviews for Aloft Chicago Downtown River North, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
Downtown Chicago
Price was CA $1,188, price is now CA $925 per person
per person
Jul. 9 - Jul. 12
Roundtrip non-stop flight included
Montreal (YUL) 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 breakfast and the helpful staff 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
Free cancellation
Reserve now, pay when you stay
The price is CA $212 per night
CA $212
per night
Jun. 6 - Jun. 7
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Grant Park and Millennium Park are located nearby. Discover genuine guest reviews for Congress Plaza Hotel, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr, Chicago, IL
Free cancellation
The price is CA $317 per night
CA $317
per night
Jun. 19 - Jun. 20
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the breakfast and the helpful staff 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.
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $205 per night
CA $205
per night
Jun. 18 - Jun. 19
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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $166 per night
CA $166
per night
Jun. 6 - Jun. 7
Stay at this 4-star boutique hotel in Chicago. Enjoy a 24-hour health club, onsite parking, and a 24-hour front desk. Our guests praise the helpful staff and the overall value in our reviews. Popular attractions Millennium Park and Navy Pier are located nearby. Discover genuine guest reviews for Hotel Felix River North/Magnificent Mile, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
The Whitehall Hotel

The Whitehall Hotel

4 out of 5
105 E Delaware Pl, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $175 per night
CA $175
per night
Jun. 19 - Jun. 20
Stay at this 4-star boutique hotel in Chicago. Enjoy free WiFi, onsite parking, and a 24-hour front desk. 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.
CitizenM Chicago Downtown

CitizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $227 per night
CA $227
per night
Jun. 19 - Jun. 20
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast, and a fitness center. Popular attractions Millennium Park and Grant Park are located nearby. Discover genuine guest reviews for CitizenM Chicago Downtown, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
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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 $920. 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.