Chicago Vacation Packages

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Top Chicago Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $1,069
per person
Dec 10 - Dec 15
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (573 reviews)
We enjoyed our stay. The apartment was spotless, and the kitchen was well-stocked with appliances and utensils. We loved the Nespresso machine! Our only disappointment was the nighttime noise from nearby trains, plus one night of loud partying below our rental. The staff was friendly and helpful. We recommend this property.

Reviewed on Sep 26, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
CA $1,692
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,502
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
The room was wonderful and the bathroom was top notch! Location was perfect. I can’t wait to stay again:)

Reviewed on Sep 26, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
CA $1,212
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (178 reviews)
Pendry Chicago

Pendry Chicago

Downtown Chicago
CA $1,348
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,146 reviews)

Where to stay in Chicago

Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

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A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

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A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

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A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

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A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

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Things to do in Chicago

Chicago is an ideal destination for families and outdoor enthusiasts alike, offering a variety of attractions such as shopping districts, arena entertainment, and theatres. Visitors can enjoy thrilling experiences like the iconic Ferris wheel and explore affordable vacation packages tailored to discover the city’s highlights. Whether you're looking for golf vacations or cheap getaway options, Chicago provides a captivating mix of activities to ensure an unforgettable trip.

Shopping

Experience vibrant shopping at Woodfield Mall, where entertainment and family fun abound. For a unique experience, visit LEGOLAND® Discovery Center, perfect for families. Gurnee Mills offers diverse shopping options in a lively atmosphere. Each location promises great finds and memorable souvenirs during your Chicago visit.

Recreation

At Wrigley Field, immerse yourself in the electrifying sports atmosphere while catching a game. The Chicago Theatre offers a blend of culture and romance with captivating performances. For a lively night out, visit the Aragon Ballroom, where you can enjoy vibrant music and entertainment in a historic venue.

Adventure

Experience the thrill of water slides and wave pools at Great Wolf Lodge Water Park, perfect for family fun. For arcade excitement, visit Galloping Ghost, where adventure vibes await. Don’t miss the stunning views from the Centennial Wheel, an iconic amusement ride that soars above the city.

Nightlife

Experience Chicago's vibrant nightlife at Dave & Buster's for a mix of drinks and entertainment, perfect for a fun night out. For live music and a romantic atmosphere, visit Kingston Mines and Blues on Halstead, both offering captivating city vibes and unforgettable experiences.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Chicago

Chicago offers a vibrant mix of family-friendly activities, outdoor adventures, and urban exploration. Visit downtown Chicago to discover top attractions like urban parks, stunning beaches, and renowned universities. Whether you’re seeking cultural experiences or fun for the whole family, there’s something for every traveller in and around this dynamic city.

  • Navy Pier: Experience the vibrant atmosphere of Navy Pier, a bustling hub on Lake Michigan. Enjoy stunning waterfront views, diverse dining options, and entertainment, including the iconic Ferris wheel. This lively destination is perfect for leisurely strolls and family-friendly activities.
  • Michigan Avenue: Known as the Magnificent Mile, Michigan Avenue offers a dynamic urban experience with high-end shopping, gourmet dining, and impressive architecture. This bustling street is a must-visit for those who appreciate city life and want to explore Chicago's vibrant culture.
  • Millennium Park: A true urban oasis, Millennium Park features beautiful gardens, public art installations, and the famous Cloud Gate sculpture. This family-friendly park is ideal for outdoor activities, relaxation, and enjoying cultural events in the heart of the city.

Best time to go to Chicago

The best time to visit Chicago is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudySlightly LowSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudySlightly LowSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyAverageAverage
April46.0°F (7.8°C)Light RainMostly SunnySlightly LowAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnySlightly HighSlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighAverage
August73.0°F (22.8°C)Light RainMostly SunnySlightly HighAverage
September67.1°F (19.5°C)Light RainMostly SunnyAverageSlightly High
October54.9°F (12.7°C)Light RainMostly SunnyAverageSlightly High
November42.3°F (5.7°C)Light RainMostly SunnyAverageAverage
December33.1°F (0.6°C)Light RainMostly CloudyAverageSlightly Low

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Stay near popular Chicago attractions

An aerial view of a baseball stadium surrounded by urban buildings.
Photo by © City of Chicago

Wrigley Field

9.0/10 (11,704 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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A modern glass building with a curved roof, surrounded by a landscaped garden and a water feature.

McCormick Place

8.8/10 (9,822 reviews)
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
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A large stadium surrounded by a cityscape with modern buildings.
Photo by © City of Chicago

Soldier Field

8.8/10 (7,063 reviews)
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
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A Ferris wheel and a carousel at a fairground.

Navy Pier

9.0/10 (24,140 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
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A large metallic sphere sculpture in a public square surrounded by tall buildings.
Photo by TM

Millennium Park

9.4/10 (30,446 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
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A roller coaster at an amusement park with autumn trees and a clear blue sky.

Six Flags Great America

8.6/10 (992 reviews)
Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.
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A cityscape at night with illuminated buildings, a river, and a bridge.
Photo by TM

Chicago Riverwalk

9.6/10 (13,574 reviews)
Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.
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A city street at night with illuminated buildings, a snow-covered sidewalk, and light trails from moving vehicles.

Michigan Avenue

9.4/10 (15,813 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.
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What to do in Chicago

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Flyover in Chicago

Flyover in Chicago

CA $53
per adult
98% of travellers recommend
Flyover in Chicago
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $63
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in Chicago

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.