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AIRBNB EXPERIENCES

Unique things to do in Chicago Loop

Book unforgettable activities hosted by locals on Airbnb.

Top-rated activities

Explore Dazzling Architecture Interiors of the Chicago Loop
Take the architecture tour voted #1 by TripAdvisor users! We will be taking a leisurely 2-hour walk exploring some of the most beautiful and often overlooked buildings in downtown Chicago, both outside and inside, and learning about the most important and interesting parts of Chicago's architectural history. Visitors often don't know where to go, or even where they're allowed. This experience takes them inside places they'd never even consider, to show off more than 100 years of architecture as it developed here in the Windy City -- including stunning stained glass, atrium-like spaces, 19th century skyscrapers, and more! Great tour for photographers and travel buffs! Some things to note: Bring a camera -- this is an AWESOME way to practice your architecture photography! Also, dress for the weather, and if it's raining, bring an umbrella. Also, please note that if you provide a non-US phone number as your day-of contact number, we **CANNOT** call you if you're lost or late!
Chicago Architecture & Highlights Tour
Chicago is known for its striking architecture, and you’ll get a chance to appreciate this on this walking tour of the Windy City. *HIGHLIGHTS* - Marvel at the stunning Chicago skyline - Discover why Chicago’s art, food and architecture is one of a kind - Get a photo opportunity in front of the world-famous “bean” sculpture *INCLUSIONS* - Popcorn tasting - A taste of a local, homemade chocolate The tour shall start under the dazzling Chicago Marquee (best known for the sign that appears in the film Chicago), before heading to the Chicago Pedway, a network of concourses, bridges and underground tunnels that locals use to get around the centre of the city. It’s the best place to escape the cities cold winters! Next, discover City Hall, where you can observe its beautiful architecture and classic interior design. Indulge in some traditional Chicago-style popcorn, before you stroll along the Chicago Riverwalk. Discover the city’s soaring skyline and most well-known buildings such as Marina Towers and the Willis Tower, before sampling another sweet treat from a local eatery. Enjoy meandering through the delightful lakefront parks along Michigan Avenue, until you arrive at Millennium Park, home to the iconic Bean Structure (don’t forget to snap a picture)!
Chicago Food Tour- Deep Roots to Deep Dish
City in a garden. Culinary paradise. From hot dogs to haute cuisine, this walking tour of the Loop is for all foodies and anyone wishing to get to know Chicago through their stomach! The Loop is the perfect spot to experience this fast-growing food scene, where locals lunch while enjoying the city’s architecture or dining under city lights that illuminate the nearby Chicago River at night. It’s the vendors and their passion for food that we’ll focus on in this neighborhood: you’ll come to appreciate the melting pot that the city has truly become, giving us the opportunity to enjoy recipes lovingly honed by generations of immigrants. Italian, German, Polish…you’ll be amazed to discover the cultural depth behind otherwise ordinary (and tasty) Chicago staples! While your local guide will treat you to some decadent deep dish pizza and other classic Chicago favorites, they might also share a seasonal offering with the freshest ingredients, perhaps even sourced by local farms. If there’s any room for more, we’ll top off your tour with a sweet snack and send you off with more recommendations for where to eat, drink, and play in this incredible city!
Lincoln Park/Lakeview Photoshoot!
Do you want some candid pictures of you and your family on your summer vacation? Or perhaps you are looking for some cute new pictures with your significant other or best friend? Or maybe you just want some cool artsy pictures by yourself for your instagram? ...No matter what your occasion is I can capture that special moment for you! I will be photographing my guests at the Lincoln Park Conservatory & then down by a scenic city view on the Lakefront (in an area only locals know about).. I want to offer an experience for tourists that can document the experience of their getaway, while offering them something off the beaten path in this wonderful city! Other things to note Wear attire that you feel comfortable & confident in!
Sketch the urban landscape with watercolors
Sketch Chicago on-location using watercolors. Capture your travels or be a tourist in your own city with Urban Sketching! Urban Sketching has an interesting history and I'll tell you about it as we walk to our sketching location for the day. Once there, we'll look at some examples from me and other artists for inspiration. I'll show you your sketch kit and talk about what to expect during your experience. Then it's time to sketch! I show you how to select your subject, use your supplies, some different ways to sketch, and ways to add color and personality. The tips and techniques I provide will help you enjoy creating a sketch. They'll also help you find your unique style. Depending on our flow, we may work on 1 or more sketches. More information: Weather permitting, this is an outdoor activity. If it's too cold, raining or snowing we will sketch indoors. I take photos of you during this experience and share with you at the end. This experience is perfect for first time sketchers as well as experienced artists. An hour before our sketch I'll send a message to coordinate our exact meeting spot downtown No experience necessary! Great for groups, dates, sightseeing, and taking in the city.

All activities near Chicago Loop

Spray 'n' Sip- Street Art & Aerosol Workshop
1. Guests join us at our space Studio W.I.P. and dive into the world of spray paint and urban art. All instruction is done by local artists. Each guest will go home with their very own piece of the mural to remember their night. 2. Upon entering guests can relax and enjoy our ever changing gallery. Feel free to bring a beverage. It's BYOB! Guests will unleash their inner street artist on a 50ft mural! This interactive workshop will turn guests into the artist and be guided along the way. Experimenting with lettering, stencils, aerosol, & cap technique guests will experience something truly unique. 3. Our main objective is to break down stereotypes that often are connected with spray paint. Guests will leave with curiosity and basic skills when applying aerosol to boot.
Explore Dazzling Architecture Interiors of the Chicago Loop
Take the architecture tour voted #1 by TripAdvisor users! We will be taking a leisurely 2-hour walk exploring some of the most beautiful and often overlooked buildings in downtown Chicago, both outside and inside, and learning about the most important and interesting parts of Chicago's architectural history. Visitors often don't know where to go, or even where they're allowed. This experience takes them inside places they'd never even consider, to show off more than 100 years of architecture as it developed here in the Windy City -- including stunning stained glass, atrium-like spaces, 19th century skyscrapers, and more! Great tour for photographers and travel buffs! Some things to note: Bring a camera -- this is an AWESOME way to practice your architecture photography! Also, dress for the weather, and if it's raining, bring an umbrella. Also, please note that if you provide a non-US phone number as your day-of contact number, we **CANNOT** call you if you're lost or late!
Signature Scent Creation
upon entering Aroma Workshop in Chicago's Lincoln Park guests are given a card to indicate which scents from our "Scent Bar" they like, then a friendly Perfumer expertly blends scents on tester strips for the guests to sample. When their favorite is picked it goes into a choice of 2.2 oz. bottles. They can even name it and we are BYOB. Couples, Mothers Daughters, Best friends all have fun creating scents together.
Explore hidden bars in Chicago
Chicago offers a lot of hidden bars for night owls. We will start the night at my favorite hidden gem in West Loop, we will spend about one hour here then head to the next bar which is an 8 minute walk. Some of the bars have secret entrances so be ready for a fun night. The bars have amazing cocktails, beers, non-alcoholic drinks, good music and a good ambiance. There are plenty of secret bars and unfortunately we cannot explore all of them in one night. However, I will share with you the location of other secret bars which you can visit later. Please be advised that drinks or food are NOT included. This is not prohibition level speakeasy tour, this is a chill bar hopping experience. I was not born in the early 1900s and don’t know anything about prohibition so don’t ask. Have a drink and relax. Please note the experience time says it lasts 3 hours but you are welcomed to stay at the bars as long as you like. If your preferred hour is fully booked, don't worry, bar fits a fair amount of people, send me a message. There are still some locations that may ask for your proof of vaccination to access the bars. Please bring it with you. A photo of your vaccination card is fine.
Gangsters and Ghosts Tours
One of the best ways to really acquaint yourself with the infamous city of Chicago is to do it from the streets, through a guided Chicago Gangster Tour or Ghost Tour, detailing the crimes, deals, and charisma that made the city what it is today. We offer a 2 for 1 deal, hosting historically-based guided tours of Chicago’s gangers AND ghost stories, right from the Chicago Loop Vice District. Other things to note Bring your camera!
Candle Making Class on Magnificent Mile in Chicago
We provide an instructor led soy wax candle making class. We provide all the supplies - soy wax, candle vessels, 19 fragrances to choose from, candle wick, jar labels, etc. We walk through them through entire process of making a candle. Added bonuses: - Parking discounted to $10 - $27 value - BYOB or complimentary wine - Shipping option if customer doesn't want to wait on the candle to cure. - 15% discount off any retail products in the store After completing your candle, it takes up to 1.5 hours to cool down. While it's cooling, go enjoy shopping and food at nearby restaurants and shops. *If you are in the last class of the day, your candle won't be ready for pick up until the following day.*
Shop Hidden Thrift Stores
A great thrifting trip is all about the thrill of the hunt! Finding the great scores happens early, so we'll get energized with coffee or a snack at our meet-up point, then take public transit to 3-4 of the best thrifting spots in Chicago and spend ABOUT an hour at each. Each spot is at top of my list when I'm looking for my next favorite item. Not only is thrift shopping great for your wallet, it's sustainable for the environment! This tour is intimate and interactive so get ready to thrift with folks who's tastes and lifestyles are completely different from your own. Making new friends is encouraged! Locals are welcome: this tour ain’t only for tourists! This is not a vintage tour. A successful thrift adventure requires vision to see the unique possibilities in an every day item - the right styling can transform something you'd initially pass up. That's where we come in! We are available to help scour the racks, give advice on how that leather jacket or platform shoes look or happy to let you do your own thing! As your experienced tour guide, I will make sure you go with a new favorite item. *If you are interested specifically in vintage finds, please check out my "Hidden Vintage & Boutique" tour on AirBnB! Other things to note Please reach out to me with questions! If you don’t arrive by CTA, I can help you snag a pass at the station together before we begin the tour.
Chicago in a Day
You’ll fall in love with Chicago and its incredible food scene combining our Chicago Architecture & Highlights Tour and Chicago Food Tour: Deep Roots to Deep Dish! *HIGHLIGHTS* - Marvel at the stunning skyline and architecture that makes Chicago so special - Explore one of the cities most historic neighborhoods - Sample some delicious food samples throughout the tour *INCLUSIONS* - 5 food stops - 5 food samples including pizza, hot-dog and popcorn tastings Beginning under the iconic Chicago sign at the Chicago Theatre, you’ll head towards the Chicago Pedway, a network of tunnels that is used by locals to get around the city. Discover City Hall, before enjoying a stroll along the Chicago Riverwalk, taking in the spectacular skyline. Feel like a local by experiencing a ride on the “L” train or water taxi (dependent on weather and time of year), whizzing past the some of the well-known buildings the city has to show. Walk the Magnificent Mile along Michigan Avenue before you enjoy the serenity of Millennium Park. Now we have built up your appetite, it’s time to get your fill of some amazing food that you will only find in the Windy city. Let’s start you off with a Chicago-style hot dog before indulging in the famous Chicago deep-dish pizza. . Explore a couple more well-known River North food establishments, before ending the tour with a classic Italian beef sandwich.
Fireworks Sailing Cruise on a Yacht
Our sailing experience begins at the Monroe Harbor Public Dock (Google maps). Boarding our 37’ luxury cruising class sailing yacht Dragonfly, a Jeanneau Sun Odyssey, we will cast off and motor out to Lake Michigan where we will set sail to a favorable course. Bring your favorite food and drinks, listen to music, relax, and take in the glittering skyline and the city’s iconic buildings from the lakefront. This tour offers an unbeatable up close and personal view of the Navy Pier Fireworks Show- on display every Wednesday and Saturday evenings Memorial through Labor Day. Do note Airbnb experiences are social, and up to 6 guests from different parties can join our standard cruise, however we welcome inquiries about private or custom outings. If you do not see a time on our calendar that works well for you, please contact us! Other things to note New friends will join your booking unless you reserve the entire boat. We only wait 15 minutes for a late guest out of courtesy for timely guests. We only cancel for lightning and will refund everyone. If you tend to get motion/seasick, or have a hangover, take motion medication 30 minutes prior.
Private Sightseeing Cruise in Chicago
What an amazing experience you will have on this One of a Kind Private Sightseeing tour! We will explore the wonders of Chicago from a 46-foot Private Yacht. Chicago's newest Harbor has been adorned with new playgrounds, swimming pools, food stands, and more. We will pick meet you here for the start of a wonderful day! After 31st harbor, we will board the amazing Italian Azimut Yacht for 3 hours of amazement. While others have ordinary boats and vessels, the Azimut is one of a kind. You won't find another in Chicago. Additionally, while others are sharing spaces with strangers, you have the luxury of your own Private Yacht for the day. We will cruise north and see the Planetarium, Shedd Aquarium, and Chicago's Skyline. Up the River, we will head to some of Chicago's finest restaurants and architecture for an hour of amazement. Only to end the day at one of Chicago's hot spots - The Chicago Play Pen. Swim, relax, listen to music and enjoy an hour together before we head back!
Taste of Chinatown Food & Walking Cultural Tour
Curious about Chinatown but unsure where to start? Let our Bobby’s Bike Hike Chinatown Food and Culture Walking Tour be your local guide on this Chicago Chinatown tour! Chicago’s Chinatown, located next door to the Loop on Cermak Street and Wentworth Avenue, bursts with colorful shops, impressive monuments, and of course, delicious restaurants. Like a Chinese menu, the sheer number of possibilities can be overwhelming. Fortunately, the experts at Bobby’s Bike Hike have created the perfect overview. You’ll sample culinary delights from five distinct Chinese regions while learning interesting facts about China and the history of Chinese immigration. Whether you’re a first-time visitor or a Chicago native, our walking culinary tour of this thriving neighborhood will whet your appetite for another visit! All food samples included in ticket price, but consider upgrading to our VIP package to include samples of plum wine, bubble tea, and a specialty jasmine Chicago craft beer only served at Phoenix Restaurant.
Nice One Day City Tour in Chicago
Welcome to the amazing city of Chicago. Check out the classical landmarks in Chicago while getting amazed by its post-modern architectures. Discover the stories behind the city’s most significant buildings such as Cloud Gate and Chicago Theatre. Take an in-depth tour of the city of Chicago and visit 360 Chicago for a full 360-degree panoramic view of Chicago from above. Explore Millenium Park and Grant Park. This tour will show you the best of Chicago in one day. This is a world’s top architecture city with bold architectures. You will take a walk in the Millennium Park, see the Cloud Gate, enjoy the urban view of the city from 360 Chicago. Itinerary: Millennium Park & Cloud Gate (20 mins) → Grant Park (10 mins) → Chicago Theater (Optional, 60 mins) → The Art Institute of Chicago (Optional, 120 mins) → Chicago Water Tower (15 mins) → Michigan Avenue (30 mins) → Chicago Cruise (Optional, 75 mins, seasonal) → 360 Chicago (Optional, 75 mins, including Tilt) We will pass by: Navy Pier, Clarence Buckingham Memorial Fountain, Marina City, Trump International Hotel and Tower, Willis Tower Observation Deck Special Notice: Some of the destinations may be closed due to Covid pandemic.Please follow your tour leader’s instruction. Your kind understanding and cooperation are highly appreciated.
Chicago limo tour with drinks, photo ops, and fun
We will meet at the Langhham building downtown to get to know each other while we wait for all the guests and limo to arrive. We will Limo party and ride all over Chicago seeing different angles of the Chicago skyline. From the Langham we will ride to Shedds Aquarium for some city skyline pictures as stop number one. After that, we will ride and check out Grant Park on the way to cruise the famous Lake Shore Drive, Michigan Avenue, and Waker Drive where will end the night one of the best nightclubs in River North This event is BYOB, bring your own beer/bottles!
Chicago Favorites Food Walking Tour
Taste your way through Chicago’s most famous recipes on this relaxing and fun Chicago food tour. In an exciting two and a half hours, you’ll feast on Chicago culinary legends such as deep-dish pizza, Italian Beef, a Chicago-style hot dog, and a delectable dessert! All food samples are included in the ticket price. You can add a VIP Craft Beer package to any ticket (over 21 please) so you can sample 3 of our favorite local craft beers (three 9oz pours). In addition to the delicious food on this tour, you will also marvel at the Wrigley Building and Tribune Tower before experiencing some of Chicago's most iconic sites along the Magnificent Mile and the gorgeous Chicago Riverwalk. Then, head into the Loop and marvel at its historic architecture as El trains rumble overhead. Walk up State Street ("that great street") with its shops and famous Chicago Theater. From there, visit world-famous Millennium Park and hear about the stories behind its landmarks, including Cloud Gate (aka the "Bean"), the Pritzker Pavilion amphitheater, and Crown Fountain. Our food walking tour of Chicago is an active, VIP adventure through town; the perfect way to see and taste the city in a single afternoon!
Chicago Craft Brewery Barrel Bus Tour
Ride in a custom engineered Barrel Bus to taste different types of craft beer on this guided brewery tour. The Barrel Bus is replete with fine wood, a barrel shape, brass and copper fixtures, a gull-wing entrance door, and headlights / taillights from a 1915 Ford Model T. Visit 3 unique breweries for craft beer samples. Learn about beer production and barrel aging from one of Chicago's best nano-breweries. Guests will enjoy 45-55 oz. of craft beer in total throughout the experience.
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