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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
ChicagoMostly Cloudy
19°C / 67°F
29mm / 1.1"
Weather data is based on monthly averages.
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Popularity rating

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This is a review for my Goway travel guide in Ho Chi Minh City. Mr. PHẠM HỮU THIỆN (TONY) was a very kind and knowledgeable guide during our 5 day stay in the city. Friendly, likeable and funny, Very accommodating to our needs during our visit. He and his driver were always early for every excursion as well as the final day for our airport departure. He gave us wonderful recommendations for sights and restaurants for our personal time. I highly recommend Mr. Pham (Tony) for your stay in the Ho Chi Minh area.George C.
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Brooke Theron has booked 3 trips for us, France and Tunisia in 2025 and we have just returned from a 2 week trip from China. The entire trip was flawless, from the research to the booking Brooke is always soo helpful in whole process. Brooke always works with us to answer any questions and make sure any request we have can be added. Our tour guides James, Helen, Felicity and Keira and drivers were all top notch with lots of information on each stop and sent us onto our next stop with no problems. The hotels, trains and tours were all excellent. We couldn't have asked for more I look forward to working with Brooke and Goway tours on our next vacation.Maddie
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Bijal and Martin (tour guide in Kenya) made this the trip of a lifetime. I felt safe every minute of the trip. I did not care for the travel from the Serengeti to Ngorogoro Crater. I felt the last hotel was too far from the crater i was exhausted not wanted to travel to the crater. The travel was absolutely brutal for 6 hoursKathie Becker
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Josie was incredible to work with. She replied to all emails quickly and effectively. She was very knowledgeable and always willing to help. Would definitely work with Josie again!! Clients had an incredible 14 days in Italy with no complaints. A dream vacation!!Chattell Blue
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Our safari in Tanzania was excellent. Brooke Theron, our Goway representative, was easy to work with, responsive and knowledgeable. Our guide in Tanzania, Anwar Razak, was outstanding. His knowledge and his driving ability was impressive. He was also engaging. We enjoyed our time with Anwar. The camps that Goway recommended were comfortable, welcoming and surprisingly luxurious while capturing the essence of the Serengeti and Ngorongoro. We had a wonderful trip. Jack B.
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My agent Lisa made the booking process easy. Her expertise on the Azores was extremely helpful. Final documents were precise and thorough. Transfers were on time, tours were informative and fun, and the lovely accommodations were well suited to our needs.Christine Hosty
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I am so happy to use Goway for my tour experience while visiting Vietnam during Oct 15 through October 29, 2026. We had 3 very good, thoughtful, and caring guides in Hanoi, Danang, and Ho Chi Minh City. They were very knowledgeable for each of their respective areas. they all fulfilled every part of our itinerary. I wish to give an extra acknowledgment to my guide in Danang and Hoi An. Mr. Phung Van Hung was very friendly and caring for me. During my stay in Hoi An, I became sick and required a visit to the local hospital in Hoi An. I contacted Mr. Phung, and he graciously offered to take me and stay with me to interpret during my visit for medical care even though he was not working that day. I really appreciate his extra above and beyond service he provided. I really must let Goway know, he is a wonderful guide!George C.
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Suzzette and her team provided exceptional support throughout our year‑long planning process for our Bali group. Despite multiple changes, updates, and last‑minute cancellations, she remained organized, responsive, and solution‑focused. Asia Trails Indonesia delivered a seamless experience from arrival to departure, and our guides, Dayu and Adit, were outstanding; prompt, knowledgeable, and attentive to every detail. The coordination across multiple departure cities, the curated excursions, and the overall flow of the itinerary were executed beautifully. My group thoroughly enjoyed the trip and is already asking about returning. I highly recommend Suzzette as a group coordinator for her professionalism, dedication, and high‑quality service.Anchored Memories Travel
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Mike K. graciously provided us with a perfect itinerary, offering us flexible high quality options for our trip. We added in a few complex details and he maneuvered around them creating smooth transitions. Planning an overseas 11 day trip can be overwhelming and Mike made everything feel easy. I highly recommend!Amy Challgren
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Goway staff was available to us throughout our entire trip to Costa Rica. Their involvement was seamless and surprisingly smooth between them and all of our hotels and tours. We have been totally impressed with their involvement with our travel agent and their complete resolution of the only problem we had during the 2 different international trips that we have taken.Diana McCrory
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