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Cityscape from Chicago River Waterfront at Dusk. Small boats and tourist ferries cruising towards the Michigan Lake

Chicago Vacation Packages and Tours

Chicago, United States

Overview

Take a trip to Chicago on your United States Vacation

Chicago is located in northeastern Illinois on the southwestern shores of freshwater Lake Michigan. The fourth-largest city in the United States, Chicago is one of the country’s most architecturally striking and culturally dynamic urban centres. The city is home to incredible museums and world-famous art galleries, delightful eateries, green parks, a stunning waterfront, and some of the world’s tallest buildings. Activities and attractions include the Magnificent Mile shopping district, Millennium Park, a Chicago River architecture boat tour, the impressive Art Institute of Chicago, and the John Hancock Tower 360-degree observation deck on the dizzying 94th floor.

Music fans flock to the city’s renowned jazz and blues scene. Sports fans come for the major sports venues, including Wrigley Field Major League Baseball stadium. The diverse music scene delivers an electrifying variety of genres, including blues, soul, and jazz, and the lively city boasts a thriving theatre, concert tour, and world-renowned performing arts scene.

Chicago is also surprisingly green, offering strolls along the Chicago Riverwalk, through the beautiful lakefront parks along Michigan Avenue, or around Museum Campus, a 57-acre park encompassing five of the city's most notable attractions, including the Adler Planetarium, Shedd Aquarium, and the Field Museum of Natural History. An expert tour guide can help navigate the city’s whirlwind of attractions and is often a local who has plenty of tales about Chicago life together with an in-depth knowledge of its character.

Dining options in the bustling city’s thousands of restaurants include everything from Chicago-style hot dogs to deep-dish pizza to Maxwell Street Polish sausages to fine dining at one of 22 Michelin-starred restaurants.

At a Glance

Languages

English

Currency

United States Dollar (USD)

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Custom Groups of 10+

Downtown Chicago Skyline
+1

Chicago: Architecture, Lakefront & Culture

Illinois, Chicago, and Cloud Gate
Discover the essence of Chicago on this VIP experience, featuring guided tours, exclusive dining, and stunning city views, from the 360 Chicago Observatory to the River Cruise.
5 days
From US$1,999/p.p.
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What do the experts say?

Aylin Esin

Aylin Esin

Team Lead
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One hidden gem is the Great Sand Dunes National Park, Colorado. Sand dunes against the backdrop of the Rockies, with sand sledding, hiking, and amazing night skies.

Most Popular Time to Travel

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Place
Conditions
Daily max temperatureMonthly rainfall
ChicagoPartly Cloudy
34°C / 93°F
55mm / 2.2"
Weather data is based on monthly averages.
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Popularity rating

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Athul Ajay was our travel agent and he was excellent from the beginning to the end of planning our trip. Great at communicating and replying back too. Sabrina Gaffoglio
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Isabella Luu made the arrangements for our trip to Scotland and all aspects of the trip and stay were excellent. Our assistance at the airports were very good as all were alerted to our needs. Our ride services were excellent. Isabella was always available to answer any questions that we had in a knowledgable and prompt manner, which is always very important to me.Audrey Henry
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Had an excellent tour of Australia, thanks to our travel specialist Katie Stephenson. She was patient as we kept modifying our plans. Got support from Goway and Katie when there was a need to rebook a tour midway through, all handled easily by Goway.Ron Preston
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We went on a highly customized comprehensive (though quick tour) of England and a bit of Scotland through Goway. Ingrid Aird did an amazing job of planning and arranging every detail with her deep experience, insight, thoughtfulness and creativity, tuning into the needs of each traveler; and she did so even though our decision to travel was rather spontaneous and last minute! Our family had the best time! We look forward to working with Ingrid and Goway again!Vilja Breiling
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We used Goway to put together an itinerary for East Africa , and Zanzibar . Everything was great and went smoothly Dawn
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I can't tell you enough how much I love to work with Callie. She is a life saver and I love how attentive she is. Every time I give her an itinerary for a client- she really knocks it out of the park with the proposal. If there are any issues- she is on it right away. Her work ethic is outstanding.Michelle Labarca
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I had the pleasure of working with Amelia on a booking for a family of 4 to Tokyo, Kyoto and Osaka. She executed everything perfectly, was attentive to needs and the family was over the top happy with their vacation. She was quick to answer questions and provide helpful feedback. Highly recommended!Jessie Williams
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We were trying to navigate Swiss Travel Center to book a 10 day train trip through Switzerland. It was exactly what we wanted but navigating their site was extremely difficult for us. Goway Travel picked up on our plight and put us in contact with Jacqueline Fagooli, one of their agents. From there on everything was so smooth. Their efficiency, communication, and thoroughness were beyond our expectations. The trip was fabulous and kudos to Jacqueline and Goway for their help in making it so.Carolyn McCormack
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We had a wonderful and amazing two weeks in North-West Scotland. Shoutout to Jacqueline at Goway Toronto and the driver/guides with Rabbie's minibus tours (Stefan and Willie). Well-chosen hotels and no worries with dietary requirements; every detail was taken care of. Thank you! Ben Daube
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