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Unusual Things to Do in Chicago

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Top Chicago Unique Experiences

Famous Tastes of Chicago Food Tour

clock 3 hours
  • Love food? Well go ahead and book this fantabulous food tour in Chicago.
  • Explore the food, history, architecture as well as culture that the Windy City is famous for. Read more
  • Pamper yourself by tasting 5 to 6 types of classic dishes of Chicago.

    • What You'll Do:

  • A walking tour offers more than enough for every traveller, as this tour can be considered a lunch tour.
  • Experience the world famous Chicago - Deep Dish Pizza.
  • For satisfying the sweet-tooth, delve into the chocolate dessert from the local bakery and cafe, after which you can take a bite of the Chicago Style Popcorn.
  • Stop at the famous Fannie May Chocolates to try several flavourful chocolates.

    • What It Includes:

  • Led by a professional local guide.
  • This food excursion is approximately 3 hours long
  • Visit six famous eateries and enjoy the food.
  • All entry tickets are included in this trip.
  • Wear comfortable shoes as the tour involves extensive walking
  • Trip is not wheelchair accessible.
  • Last minute cancellation is not permitted
  • Doesn't include hotel pick up and drop off.
  • Alcoholic beverages are not included in this tour

    • Travellers Talk:

  • Travellers liked the walking tour and were satisfied with the knowledgeable guide.
  • One of the travellers told that the food samples was of a great variety.
  • Many have commented that it's an excellent tour and they enjoyed all of the food stops as well as all of the architectural sites and their history
  • Everyone appreciated how the trip balanced the combination of delicious food tasting stops and Chicago's history.

    • Is It Right:

  • Take your taste buds on a trip that will leave you craving for more by taking part in this fun-filled journey
  • People with certain walking disabilities, are recommended not to take part in this trip
  • Read lessRead more
from€32.25 from€48.65 from€63.00 from€63.89

Chicago Craft Brewery Barrel Bus Tour

clock 3 hours 45 minutes
  • Move around town in a barrel-shaped bus that lets you taste 45 to 55 ounces of beer on this roughly four-hour trip.
  • Be provided with historical context for the recent resurgence of the craft-beer industry of this region since the 1800s, as you travel around the area. Read more
  • A variety of beer brews can be sampled at each stop

    • What You'll Do:

  • Gather at the 600 N Clark St, Chicago, IL 60654, USA.
  • Choose from different departure times, whichever is most convenient for you
  • During this ride, you can drink about 50 ounces of beer, which adds up to around 4 instant bottles.

    • What It Includes:

  • Stop over at four different breweries as part of this tour, from big names like Lagunitas to several of the city's smaller and upstart craft breweries.
  • Starting point of the tour is the same as the ending point
  • An age restriction is faced as the required age group to participate is above 21 years.
  • Suitable for a large group of adults with a maximum number of 22 people at a time

    • Travellers Talk:

  • One of the visitors liked the fact that there are multiple stops on the tour, leading to sampling different beers
  • The friendly environment that was created by the tour guide was also appreciated by many who took part
  • The fun-filled and informative nature of this trip left many tourists thoroughly entertained

    • Is It Right:

  • Take a sip and get a chance to relax completely by booking this particular trip package
  • Children are advised not to be a part of this trip
  • Read lessRead more
from€67.21 from€79.70 from€91.75

Underground Donut Tour - Wicker Park Edition

clock 2 hours
  • Taste some of the finest donuts that the Wicker Park / Bucktown neighborhood of Chicago has to offer on this 2 hour Walking Tour.  On this tour, we'll make four stops at some of the best donut spots in the city. We hope you can join...Read more
from€24.35 from€25.21 from€30.04

Chicago Scavenger Hunt Adventure

clock 3 hours
  • Turn Chicago into a giant game board with this fun scavenger hunt adventure! This challenge combines the excitement of the Amazing Race with a 3-hour city walking tour. Guided from any smart phone, teams make their way among well known and overlooked gems of the city, solving clues and completing challenges while learning local...Read more
from€18.90

Chicago Favorites Ultimate Food & Walking Tour

clock 3 hours
  • One can call this trip a perfect one, to explore the favourite cuisines and wonderful sites, across the magnificent city of Chicago
  • Stroll through the beautiful streets of downtown Chicago and taste all of the city's favourite food dishes. Read more
  • Travellers can enjoy this quintessential culinary walking tour that will help them make memories that can last a lifetime

    • What You'll Do:

  • Complete this tour with a slice of deep dish pizza, a Chicago-style hotdog, Italian beef sandwich, chocolates and pastries, as well as locally crafted beer.
  • Visit some of the most iconic landmarks, including Millennium Park, State Street and Chicago Theatre, Chicago Riverwalk, Michigan Avenue, and the Wrigley Building.

    • What It Includes:

  • Time duration of this trip is 2 hours and 30 minutes (approx.)
  • Expert professional guide will lead travellers through downtown Chicago's most iconic landmarks.
  • Guide is informative and has a really sweet and polite behaviour.
  • A maximum of 15 travellers allowed on the tour
  • The trip excludes Alcoholic Beverages - Local craft beer samples can be added for a fee
  • Excludes entry fees
  • Certain amount of fitness required to participate in the tour.

    • Travellers Talk:

  • The appreciative knowledge of the tour guide and his friendly nature made him quite popular among the tourists. Visitors liked how most of the guides knew so much about the fantabulous city of Chicago. The place also welcomes every visitor with warmth.
  • The tourist-guide helped the travellers to explore the exotic food joints. He gave quite insightful knowledge, thus helping them to learn some new facts about the Windy City.

    • Is It Right:

  • Join us! And be a part of a culinary experience that will undoubtedly make you crave for more
  • Bring your closest buddies and take part in this flabbergasting tour of food across the city.
  • Read lessRead more
from€50.57 from€51.00 from€78.29

Chicago Pizza Tour

clock 3 hours 30 minutes
  • Go ahead and book Chicago's only guided neighbourhood pizza tour.
  • Travel along off-beaten path into Chicago's neighbourhoods to enjoy the best pizza. Read more
  • A comprehensive tour where travellers can learn the science behind ingredient selection and baking. Also, in this tour, visitors can sample slices from historic pizzerias.

    • What You'll Do:

  • Stop by the Magnificent Mile of North Michigan Avenue to enjoy a special pizza
  • Next visit the Flo & Santo's eatery where you can hop on to Chicago's thin crust tavern style pizza.
  • Get a chance to enjoy the burnt cheese caramelized crust with the sweet sauce at Pequod's, that has been a local legend since 1971.
  • Grab a bite of the famous Piece Pizza that was one of the first non-regional styles to set up, in the Chicago neighbourhoods.

  • What It Includes:

  • Follow tour local guide around for this trip.
  • Food excursion is approx. of 3 hours and 30 minutes
  • All entry fees are included in this trip package.
  • Transportation is by air-conditioned mini coach
  • Operates in all weather conditions.
  • Children under 6 are free so please inform the organizers .
  • Four slices of pizza for each person are included in this trip.
  • Isn't wheelchair friendly and most travellers can participate.
  • Doesn't include hotel pick up and drop.

  • Travellers Talk:

  • Tourists liked the tour guide, found it excellent. He knew the history of Chicago Pizza like the back of his hand. His anecdotes about Chicago, and the history of pizza were fantastic.
  • One traveller said that he liked the tour and the overall tour experience

    • Is It Right:

  • If you also are a lover of Pizza, then not booking this tour will be a complete waste of time in case you are in Chicago
  • Other than certain exceptions, this trip welcomes the participation of most travellers
  • Read lessRead more
from€42.05 from€53.59 from€70.76 from€81.98

Chicago Style Food Tour

clock 3 hours
  • Come join a walking tour that lets you discover the culinary side of Chicago
  • Immerse yourself in the deliciousness of Chicago style food Read more

    What You'll Do:

  • Trip begins at 864 N State St, Chicago, IL 60610, USA and the first stop of the tour is Pizano's Pizza & Pasta, 864 N State St, Chicago, IL 60610, USA
  • Get to taste the traditional deep dish pizza of Chicago at the Pizano's Pizza & Pasta
  • Drop by at the Downtown Dogs in 804 N Rush St, Chicago
  • Enjoy a classic Chicago hot dog at the Downtown Dogs, then head towards Cafe L'Appetito in 3332 N Broadway
  • Near Cafe L'Appetito is the local treasure market where you get to treat yourself to sweet delights, after which , visit the Chicago Kernel Gourmet Popcorn, Millennium Station, and then head towards Fannie May, 343 N Michigan Ave which houses different chocolates
  • Billy Goat Tavern, Lower, 430 N Michigan Ave is the last destination of this tour
  • The day ends at 151 E Randolph St, Chicago, IL 60601, USA

    • What It Includes:

  • The tour lasts for about 3 hours
  • A professional tour guide will be provided
  • Tourists will get a chance to visit a network of walkways which is situated underground, for a round of good snacking
  • A block away from the Magnificent Mile tourists indulge in eating Chicago Style Hot dog

    • Travellers Talk:

  • The tourists got to visit a variety of spots and got to taste a lot ot food
  • Information about the history of the places travellers visit leaves them thoroughly entertained
  • They found the tour guide knowledgeable and friendly and liked the services that they provided

    • Is It Right:

  • If you love food as much as the next person, then booking this tour shouldn't be a problem
  • Take part and visit restaurants as old as 60 years like the Pizano's Pizza and Pasta
  • Read lessRead more
from€46.49 from€55.00 from€59.00 from€62.98 from€65.83

Chicago Walking Food Tour With Secret Food Tours

clock 3 hours
  • Come and be a part of a walking tour of 'Chicago Loop " and also taste some exclusive cuisines of Chicago.
  • Discover some hidden gems and great stories about the city. Read more
  • Tour also includes world-famous Italian beef sandwich with delicious dips, which was invented in Chicago.

    • What You'll Do:

  • Grab a bite at the renowned eateries and shops and drop by various theatres as well as parks.
  • Catch a glimpse of the riverside pedestrian path featuring city views, bridges, fishing piers and boat docks.
  • Stop by at one of the world's tallest buildings found here in America

    • What It Includes:

  • Tour time is approximately of 3 hours
  • Led by a local guide
  • Maximum of 12 people will be allowed for this tour
  • Food tasting and lunch is included in this tour.
  • Confirmation of the tour is received at the time of booking.
  • Requires a good weather. If the trip gets cancelled due to bad weather, then you will get full refund of your money.
  • Pick up and drop off are not included in this tour.
  • Moderate physical fitness level is required for this tour.

    • Travellers Talk:

  • One of the tourist said that the tour guide was wonderful, knowledgeable, professional and funny.
  • Highly recommendable walking tour by many visitors.
  • The food and the tour itself was liked by all who took part
  • Many liked the various interesting sites that they saw and learned about the city, in addition to food sampling.
  • Some travellers said that the guide was knowledgeable and the food samples were delicious. The secret restaurant was amazing.

    • Is It Right:

  • If you want a tour that is the perfect combination of food and travel, then book this one right now!
    • Participation of most travellers, except people with some kind of walking disability, is allowed
  • Read lessRead more
from€32.25 from€73.79 from€200.19

Chicago Delicious Donut Adventure by Underground Donut Tour

clock 2 hours
  • An underground donut tour, which is Chicago's first donut tasting tour
  • The tour takes the tourists to Do-Rite Donuts & Coffee, The Loop and many other famous stores that are popular for their donuts Read more
  • Visit Firecakes Donuts & Doughnut Vault to enjoy the delicious taste.

    • What You'll Do:

  • The tour begins at the Do-Rite Donuts & Coffee where the tourists get to taste some tasty donuts and stay there for 30 minutes
  • Loop tourists visit 4 different stores to taste donuts
  • The next stop is Doughnut Vault where the tourists stop for 30 minutes and enjoy the sample donuts
  • A 30 minute stop is given at the Firecakes Donuts where tourists get to taste the dulcet donuts
  • The last stop is the Stan's Donuts & Coffee where tourists get more tasty doughnuts to satisfy their appetite.
  • Additional donuts are purchasable at each stop

    • What It Includes:

  • Time duration for this trip is 2 hours. One gets to pop in as well as pay a visit to various doughnut shops in Chicago
  • Travellers get to taste the samples of marvellous doughnuts for this tour.
  • Moderate physical fitness is required for all travellers who take part in this tour
  • The tour claims to give the money back if the tourists do not enjoy the tour and are not satisfied with their experience.

    • Travellers Talk:

  • The tourists said there were plenty of doughnut samples to taste from
  • They got plenty of information during this tour that were unknown to them previously.
  • Those attending the trip get to know exciting facts about the city's history
  • The tourists said it is a good activity for doughnut lovers

    • Is It Right:

  • This is a perfect tour for travellers who also go by the name "Donut lovers
  • Unless someone has certain dietary restrictions, this is a trip worth spending one's time and money in.
  • Read lessRead more
from€24.35 from€24.74 from€36.00 from€62.64

Gangsters and Ghosts Tour in Chicago

clock 2 hours
  • Interested in exploring Chicago from the perspective of ghosts and gangsters? Want to really immerse yourself in the history of this great American city, right from the locations that started it all? This tour visits the locations frequented by some of Chicago's most notorious gangsters along with many of the most haunted locations in...Read more
from€22.27 from€31.00 from€32.24

Adventurous Scavenger Hunt in Chicago by Zombie Scavengers

clock 1 hour
  • Zombie Scavengers takes you on an adventure in Chicago to survive the zombie apocalypse! Use our app and some strategy to find a list of items needed to survive, in any order you'd prefer, around the city. Find the survival items to get points and do fun zombie themed challenges for points as well. Contrive a plan to get your survival team the...Read more
from€18.42

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

clock 4 hours
  • Come and take part in one of the most mouth-watering tours in the city and taste some of the flavourful dishes of Chicago
  • A fully guided motorbike tour can also help travellers to explore the city of Chicago Read more
  • Get a taste of the celebrated craft beer and don't worry about the glass count as one get to try more than one glass during this tour

    • What You'll Do:

  • Get a chance to try some of the authentic and traditional dishes of Chicago
  • Extending for 14 miles, the trip involves tasting the flavoursome comestibles which include dishes like deep dish pizza, Chicago style hot dog, etc
  • Among the sweet dishes there are also gourmet cupcakes
  • You should not miss out the different varieties of craft beers
  • Have a wondrous experience of the beautiful nothern side of Chicago on this tour

    • What It Includes:

  • It is a 4-hour long tour
  • Follow an expert guide throughout this tour
  • Bicycle and helmet are inluded in the trip
  • Water bottles are also provided
  • Try out the exotic cuisines and sample a few brews.
  • Some heavenly Beer samples are provided to the tourists for tasting
  • Any children or infant on this tour need proper supervision of their parents.

    • Travellers Talk:

    The tourists loved the tour and were delighted to see the Northern part of Chicago. They even loved the classic food of the land.
  • Travellers said that the bike rides were safe and they liked the exciting eatables during the tour.
  • They found their guide to be very enthralling due to the excellent services provided by them. They also liked the taste of the local beer.

    • Is It Right:

  • Absolutely! This trip will truly leave anyone taking part with a happy smile
  • An ideal trip for all food and beer lovers
  • Read lessRead more
from€35.70 from€66.00 from€67.21 from€81.98

Chicago West Loop Pizza Crawl

clock 3 hours
  • Taste four different styles of pizza in about three hours. Learn about Chicago's 10 pizza styles, and discover why there's more to The Windy City than just deep-dish. Go back in some of the kitchens to see how pizzas are made, and taste the differences. Expert doughcents will share the history of Chicago pizza as well other interesting tidbits...Read more
from€72.77

Private Vacation Photography Session with Local Photographer in Chicago

clock 1 hour
  • Flytographer Private Vacation Photo Shoot

    Connect with a local hand-picked professional photographer in Chicago and capture your most memorable moments during this private photo shoot. Get insider tips on the best things to do in Chicago, including where to eat & what to see from your vacation photographer. Return from your trip with...Read more
from€231.14 from€240.00 from€275.43

Downtown Chicago Walking Pizza Tour

clock 2 to 3 hours
  • This tour is just a short walk through great Chicago neighborhoods starting near Navy Pier and the Magnificent Mile, and then heading into the Gold Coast & River North. Compare two American pizzas vs. two Italian pizzas to understand how pizza evolved as an immigrant food. Explore Deep Dish, Roman, Neapolitan, and Artisanal pizza in just a couple...Read more
from€51.89 from€51.89 from€63.56