Chicago Vacations 2025 from CA $877

Chicago flight + hotel packages

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

Ambassador Chicago, part of JdV by Hyatt

Downtown Chicago

per person

Feb. 23 - Feb. 28

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Chicago (ORD)

Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.

Waldorf Astoria Chicago

Downtown Chicago

Save 100% on your flight

per person

Feb. 23 - Feb. 28

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Chicago (ORD)

Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Millennium Park are located nearby.

Hotel Riu Plaza Chicago

Downtown Chicago

per person

Feb. 23 - Feb. 28

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Chicago (ORD)

Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Millennium Park are located nearby.

Virgin Hotels Chicago

Downtown Chicago

per person

Feb. 23 - Feb. 28

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Chicago (ORD)

Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a nightclub, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Millennium Park and Michigan Avenue are located nearby.

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

Downtown Chicago

per person

Feb. 23 - Feb. 28

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Chicago (ORD)

Stay at this 4.5-star luxury hotel in Chicago. Enjoy 2 restaurants, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Millennium Park 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 $134

CA $157 total

includes taxes & fees

15 Jan - 16 Jan

Book a stay at this 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 Michigan Avenue 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 $141

CA $165 total

includes taxes & fees

26 Jan - 27 Jan

Stay at this 4-star 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 Millennium Park are located nearby.

Hyatt Regency Chicago

151 East Wacker Dr, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $207

CA $286 total

includes taxes & fees

31 Jan - 1 Feb

Book a stay at this eco-certified hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Millennium Park are located nearby.

Free WiFi

Restaurant

River Hotel

75 East Wacker Drive, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $138

CA $162 total

includes taxes & fees

19 Jan - 20 Jan

Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Millennium Park are located nearby.

Pet-friendly

Free WiFi

Hilton Chicago

720 S Michigan Ave, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $176

CA $249 total

includes taxes & fees

18 Jan - 19 Jan

Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Michigan Avenue are located nearby.

Pendry Chicago

230 North Michigan Avenue, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $230

CA $330 total

includes taxes & fees

9 Feb - 10 Feb

Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Millennium Park and Michigan Avenue are located nearby.

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.

Popular places to visit

Magnificent Mile - River North which includes signage, a city and night scenes

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.

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.

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 theater 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 $877. 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.