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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)

What do the experts say?

Aylin Esin

Aylin Esin

Team Lead
Learn More About This Expert
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
ChicagoLight Rain
31°C / 88°F
64mm / 2.5"
Weather data is based on monthly averages.
-
Popularity rating

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While researching suppliers for a clients Thailand honeymoon, I remembered being referred to GoWay by a longterm TA ….because they “get it right and get it done!” I had already started their training modules, so I put in a quote. Immediately, Taylor responded with a very thorough email and we decided to chat. I gave him my specifics and he again responded immediately and matched my client’s travel needs 100%. I found it comforting to speak with a country expert with the knowledge I needed. My clients booked their vacation and are very excited about their itinerary! Thank you Taylor for making this process seamless.Karla B
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The most amazing experience with Goway!! Phoebe did an amazing job planing the best trip to Paris, Florence and Venice with a great mix of relaxing and adventure days. Will be recommending to other travellers. Always someone available which is great when you are travelling in different time zones. Overall cannot be more happy with our experience working with Goway Lauren Bouw
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Our rep at GoWay, Kimberly, was fantastic from start to finish. She came up with the exact itinerary we wanted for Melbourne, Uluru, Cairns and Sydney, and assisted us with both international and domestic flights to help us get the best rates. Once we were on the trip, everything flowed seamlessly and every tour and transport was on time.Lisa Wildes
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As a travel agent, this is not the first time I’ve chosen to work with Goway for organizing my clients’ trip, this time to Chile, and once again, the experience was outstanding from start to finish. Throughout the entire process, I could count on truly professional service from Susanna. My clients are very experienced travelers and requested a highly customized itinerary, including many unique experiences that are not typically included in standard tour programs. There were also several occasions when, on behalf of my clients, I requested changes to an already prepared itinerary. Susanna was consistently helpful, patient, understanding, and — just as importantly — incredibly kind and pleasant to work with. It was clear that she genuinely cared about creating the best possible experience for my clients. I’m also certain that much of the work she put in went well beyond standard hours and expectations. My clients returned absolutely delighted with their vacation, which is always the greatest confirmation of a job well done. Thank you, Susanna, for your dedication and exceptional support. And thank you, Goway, for another wonderful experience!Beata
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Our family trip to Machu Picchu was absolutely incredible, thanks to RuthAnne Leonty. Every tour was thoughtfully organized and the guides were top-notch. The private transportation and transfers were flawless, making everything run smoothly with zero stress from start to finish. Not a single hiccup...just an amazing experience!Barb
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We booked our 3,week tour of Vietnam, Laos and Cambodia and overall it was an excellent experience. I typically book my own travel, but travelling with a group and wanting tours in each destination made GoWay a great choice. We had great hotels and good guides in each city. I will say that our standout guide was Romeo Tran in Ho Chi Minh City. We spent a few days in the city, as well as an over night boat ride on the delta, and he was fantastic. We had alot of fun with him, and would highly recommend him in particular. Neil Braun
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We booked a Viking cruise (Venice to Athens) through Goway Travel and it was fantastic! Our agent Kimberly was extremely helpful with air travel options, choosing excursions, and suggestions for pre and post cruise activities. Great communications and a really enjoyable experience.Stanley
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We booked through Paula Williamson in the Toronto office, a Great Journeys New Zealand trip and it was fantastic! Although I had already scheduled a trip on The Ghan train in Australia, Paula helped me work it all as one huge 45 day trip including Bali Indonesia. My favorite was the New Zealand trip as I’d never been there before and the tour guide Toni was so spectacular and caring. I’m so pleased Goway was involved and I didn’t require any additional assistance once We'd started the first flight March 8. If we do another overseas trip, Goway will be involved.John
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