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Specialty designed tours & experiences to help create your ultimate trip to Chicago
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Our passionate team have carefully curated Chicago Tours to suit any vacation. We're adding new tours in Chicago monthly, so keep checking back to see our new excursions!
Chicago Foodie Tour: Windy City Favs
4 hoursUS$269 US$239
Chicago Instagram Walking Tour
4 hoursUS$229 US$199
Chicago Loop Architecture Private Walking Tour
3 hoursUS$179 US$159
Chicago Instagram Tour: The Most Famous Spots
6 hoursUS$689 US$599
Chicago Downtown Highlights Private Walking Tour
4 hoursUS$199 US$189
Chicago Historic Pullman Company Town Private Walking Tour
4 hoursUS$199 US$189
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Planning Your Vacation to Chicago
Be prepared to be blown away by Chicago, the Windy City will whisk you off your feet with an array of architecture, a flurry of music festivals and a sensational selection of restaurants. With so much going on in one city, our tours in Chicago, Illinois are some of our most popular tours in the United States. We’d love to have you join us on one of our amazing tours in Chicago and let us help you explore this expansive city. Take a look at our Instagram Tour in Chicago which embraces all of the best, most remarkable landmarks in Chicago. If you’re a fan of fine food then our Chicago Foodie Tour will absolutely hit the spot!
Why take a vacation to Chicago?
Vacations to Chicago and our Chicago tours attract many types of visitors. The city is so varied, it really does have something for everybody and our tours encompass the culture and beauty the city has to offer. Think museums and music, art and architecture, sport and shopping, beaches, breweries, parks and pizzas.
Fancy hitting the beach? Yep, Chicago’s 26 beaches are pretty epic. The water of Lake Michigan can be cold but there are plenty of beach and water sports to help you work up a sweat. In the summer season there are an abundance of festivals from Blues to Rock, there isn’t a park that doesn’t host some kind of shin-dig. Speaking of parks, Chicago boasts lots of green space as a distraction from the high rises, there are over 550 parks in fact.
Sport is a big thing in Chicago. Watching a local game is a must, you’ll not meet many locals who don’t follow or support either baseball or football. Our Chicago tours will take you to Wrigley Park, home of the Chicago Cubs, one of the city's two Major League Baseball clubs.
Whoever you are traveling to Chicago with, family, friends, on a couples trip or visiting on your own, our guided tours of Chicago offer something for every type of traveller. We’ll whisk you to the Magnificent Mile for a spot of shopping, visit the Navy Pier and stroll along the beautiful Chicago Riverwalk. For a truly unforgettable experience of Chicago, book your tour with us today and take advantage of our local tour guides!
What to pack for Chicago
- Comfortable Shoes - Comfortable shoes are a must in Chicago. With so many attractions in this city to see on foot, you will find that you will spend a lot of time on walking tours in Chicago!
A lightweight jacket - The city has 4 very distinct seasons however we think it’s a good idea to have a lightweight jacket, preferably waterproof just in case it gets chilly or rains at night.
Plug adapter - We all rely on our phones more now than ever. Maps, directions, recommendations, as well as keeping in touch with those at home and of course, taking pictures. Having a plug adapter compatible with the USA plug socket is vital.
Portable Charger - As well as your plug adapter it might be a good idea to have a portable power bank with you in case your phone battery dies just as you’re snapping one of Chicago’s many hot spots.
- Sun Tan Lotion - Chicago has 4 seasons, however, it is always advised to pack your sun tan lotion no matter what time of year you’re travelling.
An over-the-shoulder-bag - Having a comfortable bag to carry with you each day is key in Chicago. Phone, camera, purse or wallet and maybe a water bottle, a sturdy bag with good shoulder straps will save any unwanted discomfort.
Frequently Asked Questions
Is Chicago safe to visit?
Yes, absolutely. Of course it’s wise to practice basic precautions, for example, don’t venture into an unknown neighborhood on your own but generally speaking, Chicago isn’t a dangerous place to visit.
Why is Chicago called the Windy City?
This is a bit of a tough one to answer because the origins of this nickname are not very clear. The most obvious answer would be because of cold winds that blow off of Lake Michigan and sweep through the city. However, it’s certainly not the windiest city in the USA. Another theory is that it is a reference that dates back to 1983 when Chicago’s politicians were said to be full of hot air. Why don’t you ask our friendly guide when you’re on one of our Chicago tours and see what a real local thinks?
Does Chicago get tornadoes?
Chicago is an area that is prone to tornadoes. The city is well equipped with advanced warnings if a tornado is due. Tornadoes have been known to be most common in the springtime with often a peak again in the late summer through to autumn.
What’s the best way to travel in Chicago?
The short answer to this is walking! Chicago is one of the most accessible cities by foot. Traffic can get very busy in Chicago so if you’re looking for a relaxed vacation we don’t advise you to drive. Chicago has L trains which are above and below ground and weave their way through the city transporting you to all the sights you’ll want to visit. If you’re staying for a few days or more it’s best to get a rechargeable Ventra Card which can be used on subway trains, buses, and Metro Trains. Simply tap it as you board and you’ll save around $0.75 per journey compared to a standard fare.
Is Chicago expensive to visit?
As with most places Chicago can be as cheap or as expensive as you make it. There is a varied choice of hotels with the average cost per couple being $304 per night, but you will find cheaper and can certainly push the boat out and spend much more. The average cost of a meal in Chicago is $24 but again with such a vast selection of delicious restaurants this price will vary. There are lots of things to see and do in Chicago for free, especially in the warmer months, so it is possible to experience the Windy City without spending a fortune everyday.
Wherever stage you’re at when it comes to planning your vacation to Chicago, we hope we’ve given you some tips and tricks to help you make the most of your getaway. If you’re still stuck for things to do, consider taking a couple of our private tours in Chicago and enjoy getting to know the Windy City!