Chicago Vacations 2025 from CA $939

Chicago flight + hotel packages

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

Hilton Chicago

Downtown Chicago

Save 100% on your flight

per person

Jun. 6 - Jun. 9

found 13 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

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 Soldier Field and Chicago Riverwalk are located nearby.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

per person

Apr. 24 - Apr. 27

found 15 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

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

Pendry Chicago

Downtown Chicago

Save 100% on your flight

per person

May 5 - May 8

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

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 Chicago Riverwalk and Michigan Avenue are located nearby.

Level Chicago - River North

Downtown Chicago

Save 100% on your flight

per person

May 29 - Jun. 1

found 2 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

Stay at this 4-star 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.

Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Save 100% on your flight

per person

May 5 - May 8

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

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 Chicago Riverwalk are located nearby.

Top Chicago hotels deals

River Hotel

75 East Wacker Drive, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $141

CA $166 total

includes taxes & fees

6 Apr - 7 Apr

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 Chicago Riverwalk and Michigan Avenue are located nearby.

L7 Chicago by LOTTE

225 N Wabash Ave, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $212

CA $249 total

includes taxes & fees

27 Mar - 28 Mar

Book a stay at this boutique 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 Chicago Riverwalk and Michigan Avenue are located nearby.

The Westin Michigan Avenue Chicago

909 North Michigan Ave, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $169

CA $235 total

includes taxes & fees

20 Apr - 21 Apr

Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, 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 Chicago Riverwalk are located nearby.

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $164

CA $193 total

includes taxes & fees

24 Mar - 25 Mar

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 Chicago Riverwalk and Soldier Field are located nearby.

Crowne Plaza Chicago West Loop by IHG

25 South Halsted Street, Chicago, IL

Free cancellation

CA $141

CA $165 total

includes taxes & fees

30 Mar - 31 Mar

Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Chicago Riverwalk and United Center are located nearby.

Hilton Garden Inn Chicago Downtown/Magnificent Mile

10 E Grand Ave, Chicago, IL

Free cancellation

Reserve now, pay when you stay

CA $152

CA $179 total

includes taxes & fees

13 Apr - 14 Apr

Stay at this 3-star 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 Chicago Riverwalk are located nearby.

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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

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 acclaimed art scene 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 art scene and notable monuments in this vibrant area.

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.

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 $939. 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.