Chicago Vacations 2026 from CA $767

Chicago flight + hotel packages

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

Level Chicago - River North

Downtown Chicago

CA $767

per person

May 7 - May 10

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,281

per person

Jun 4 - Jun 7

found 17 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

CA $1,320

per person

Jun 4 - Jun 7

found 17 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Level Chicago Fulton Market

Downtown Chicago

CA $1,165

per person

May 18 - May 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Chicago (ORD)

Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

CA $1,338

per person

Jun 4 - Jun 7

found 17 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

Book a stay at this boutique hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Top Chicago hotels deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $165

CA $194 total

Mar 27 - Mar 28

includes taxes & fees

Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.

Free WiFi

Restaurant

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $166

CA $195 total

Mar 22 - Mar 23

includes taxes & fees

Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Pool

Breakfast included

Hotel Riu Plaza Chicago

150 East Ontario Street Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $179

CA $249 total

Mar 30 - Mar 31

includes taxes & fees

Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Breakfast included

Free WiFi

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $141

CA $166 total

Mar 22 - Mar 23

includes taxes & fees

Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Pool

Pet-friendly

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $267

CA $313 total

Apr 3 - Apr 4

includes taxes & fees

Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and The Dome at the Parkway Bank Sports Complex are located nearby.

Free airport shuttle

Pet-friendly

Eurostars Magnificent Mile

660 North State Street Chicago IL

Free cancellation

Reserve now, pay when you stay

CA $196

CA $230 total

Mar 17 - Mar 18

includes taxes & fees

Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Spa

Free WiFi

Don't see what you're looking for?

See all available properties in Chicago

View all properties

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

Wrigley Field

4.5/5(158 reviews)

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.

Michigan Avenue

4.5/5(19 reviews)

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.

McCormick Place

4.5/5(141 reviews)

During your trip, find out what's happening at McCormick Place, a top convention center in Chicago. Discover the acclaimed art scene and notable monuments in this vibrant area.

Frequently asked questions

How much are vacation packages to Chicago?

Get ready to be surprised — you can vacation in Chicago for as low as CA $767. 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 56 kilometers from Chicago.

Which airport is best for Chicago?

O'Hare Intl. Airport (ORD) (26 kilometers away from downtown), Midway Intl. Airport (MDW) (14 kilometers away from central Chicago) and Lewis University Airport (LOT) (48 kilometers 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.