Chicago Tours & Trips 2025 / 2026

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Look down on the city from the Willis Tower Skydeck
Experience the city from a new point of view – literally. As the second-tallest building in the US, the Willis Tower Skydeck is the ultimate way to see the city. Jump on a walking tour and learn about some of the city’s most iconic buildings while looking out at them from the 103rd floor. If you’re game, The Ledge is the place for some pretty epic selfies. Walk out on the glass plane that juts out beyond the walks of the building, towering a whopping 412 metres above the streets. To beat the crowds and experience the skyline at night, show up during the Skydeck's evening hours.
Check out concerts and public art at Millennium Park

Chicago is bursting with culture year-round, but it really comes to life during the summer months. Many of the concerts and public events happen in Millennium park, which has become one of the centres of artistic and creative life in the city. Home to iconic public art installations such as Cloud Gate and Crown Fountain, enjoy the amazing design of this public space while enjoying some seriously good tunes at one of its many public concerts. Keep your eyes out for free movie screenings that take place on the lawn at Jay Pritzker Pavilion, or skate over the McCormick Tribune Ice Rink during the winter months.
See animals (for free!) at Lincoln Park Zoo

Us travellers love a bargain, so we know to send them your way. The Lincoln Park Zoo is one of the best free things to do in the city. With more than 1,000 critters to be seen each and every day, gawk over cute penguins and pretty pink flamingos in this typical American walk-through zoo. Be sure to check the massive Regenstein Macaque Forest, where you can make friends with snow monkeys, as well as the historic McCormick Bird House, where hundreds of colourful birds zip around. If you prefer to enjoy the animals from a bit of a distance, grab a caffeine hit at Café Brauer, where the coffee will eventually turn into cocktails as the day progresses.
Go crate-digging for records at Dusty Groove

Discover some of the old 70s soul in Wicker Park, Chicago. Dusty Groove is one of the coolest places in the city, home to thousands of old-school records. Specialising in Afrobeat, jazz, reggae, soul and blues albums, ask the sales assistants about these distinctive genres and they’ll point you in the way of some obscure titles. Don’t have much room in your suitcase for a couple of extra LPs? Dusty Groove also sells coffee, so grab a cup and spend some time chilling out to the sounds of some smooth vinyl.
Take in late-night jazz at the Green Mill

There’s a reason Chicago loves jazz so much – in the 1920s, the city was a hot-spot for gangsters like Al Capone, who would frequent the Green Mill and listen to some of the swinging beats. Restored to its original splendour in the 1980s, the Green Mill is still the place to go for some old-school flavour. With live musical performances every night, catch a show from B-3 organ players, jazz vocalists and classic big bands. Grab a cocktail, take a snap underneath the iconic glittering sign and dance the night away. But do get there early, as this place always packs out.

Things to do in Chicago

Taste of Chicago
Culture & Music

Foodies, get excited: Taste of Chicago is one for you. As the premier outdoor food festival oif the US, Taste of Chicago is a showcase of the diversity of flavours in the city. With an incredible array of food available, the festival also has featured musicians that add major good vibes to the event. The Taste of Chicago happens every American Summer at Grant Park.
Lincoln Park Wine Festival
Wine & Food

Who doesn’t love a good vino? Chicago sure does. It’s annual Lincoln park Wine Festival is a celebration of everything wine-related. Discover more than 80 varieties of wine from an array of producers and participated in one of the ticketed tastings. With food and art also on offer, class it up at the Lincoln Park Wine Festival every May.
Mayfest - Music & Culture

Happening on one of the last weekends of May each year, Chicago’s Mayfest is the annual kick-off event for the summer festival season. With multiple stages featuring some of the city’s best music, artists and entertainment, enjoy the good vibes of this event with food and beer in hand. Tickets are also super cheap, usually around the $10 mark.
Chicago Jazz Festival

Known for its eclectic program and general good vibes, the Chicago Jazz Festival is a Labour Day Weekend tradition. Usually occurring at the end of August or early September each year, this music festival aims to promote awareness and appreciation of the genre and for its musicians. The festival includes series of free jazz performances for people of all ages to enjoy.
Chicago Auto Show
Sport

Rev heads and car enthusiasts, get excited: Chicago is home to the biggest Auto Show in North America. Put on in February every year by the Chicago Automobile Trade Association, the Auto Show takes place in the McCormick Place complex. At the show, you’ll find a showcase of domestic and imported passenger cars and trucks, sport utility vehicles and experimental or concept cars.

Top 5 Festivals in Chicago

As a city with a love for food, wine and culture, there’s always something exciting happening in Chicago. Enjoy a glass at the Lincoln Park Wine Festival, catch a free performance at the Chicago Jazz Festival or learn about the latest auto innovations at the Chicago Auto Show – here’s what to do in Chicago.

Field Museum of Natural History

Founded to house the biological and anthropological collections of the World Exposition of 1893, this massive natural history museum tells the story of human and animal life from around the world. Check out dinosaur bones, learn about Egyptian Pharaohs and discover Ancient China at the Field Museum.
Museum of Science and Industry

The Museum of Science and Industry is one of the largest centres of science in the world. With exhibits that involve a mirror maze, restored U-505 German submarine, a simulated coal mine and vintage trains, this interactive museum will let you set your inner-kid loose.
Art Institute of Chicago

Guarded at the entrance by the iconic bronze lions, the Art Institute of Chicago is a must for art lovers. Boasting over 300,000 artworks and artefacts from all over the world, learn about German expressionism one minute and ancient China the next. Be sure to check out the Throne Miniature rooms and the work of renowned architect Frank Lloyd Wright.
Adler Planetarium

With interactive displays and amazing light shows, who doesn’t love a planetarium? The Adler Planetarium is one of the best, featuring virtual-reality trips through space and time. Staffed by world-class researchers, be sure to pick their brains during the tour. For some after-hours adult fun, check out the monthly Adler After Dark parties.
Museum of Contemporary Art

Contemporary art museums are always the most fun – and Chicago’s is no exception. This museum houses one of the largest collections of modern art in the US. Discover masterpieces by local artists, catch a workshop or curated discussion, or simply chill out in the stunning gardens. If you want to get a bit fancy, Marisol, the museum’s in-house restaurant, is also a great place for an inspired bite.

Top 5 Museums & Galleries in Chicago

History, art and science abound in Chicago. Learn about war planes one minute and dinosaurs the next. Here are our top-five favourite Chicago museums, where you can catch an artist discussion, go on a virtual-reality tour of space, or hang out in some manicured gardens.

Pizza puffs
Cheesy, crispy and delicious, pizza puffs are Chicago’s answer to pizza-for-one. Much like a traditional Italian calzone, these golden pockets of pizza are deep fried to perfection. Once you bite into the crunchy crust, the melted cheese oozes out. *Drool.* Pick up a pizza puff at Albano’s Pizzeria in Cicero.

_{Best eaten at}
_{Albano's Pizzeria, 5913 W Roosevelt Rd, Cicero, IL 60644}
Cheeseburger
Americans love a cheeseburger, but this bad boy has been hailed as the country’s best. At Au Cheval diner, the burgers are made up of thin patties topped with melted cheese, Dijonnaise sauce and housemade pickles. Slap on some extra fried egg, bacon and even a slab of foie gras to this dream burger. Run, don’t walk.

_{Best eaten at}
_{Au Cheval, 800 W Randolph St, IL 60607}
Chorizo-stuffed Medjool Dates
Avec Restaurant has been one of Chicago's most popular eateries for a long time. Trust us when we say that this dish will change your Whole. Damn. Life. Stuffed with chorizo, wrapped with bacon and served with piquillo pepper sauce, medjool dates never looked so good.

_{Best eaten at}

_{Avec, 615 W Randolph St, IL, 60661}
Smoked salmon
Being located on the shores of Lake Michigan, Chicago and seafood go hand-in-hand with smokehouses. A dying art, Calumet Fisheries is the spot delivering some of the best fish in town. You can’t go past their smoked salmon. It’s so good you can eat it straight off a cracker.

_{Best eaten at}
_{Calumet Fisheries, 3259 E 95th St, IL 60617}
Cemita Atomica
You’ve never had a sandwich like this before. Cemitas Puebla brings Mexican street food to the masses in Chicago. Our pick? The Atomica. Stuffed with carne enchilada, milanesa and jamon on chewy, freshly-baked bread, every bite is seriously satisfying. If you don’t want to be stuck in a food coma, maybe split this one with a mate.

_{Best eaten at}
_{Cemitas Puebla, 817 W Fulton Market, IL 60607}

Food in Chicago

With Italian, Mexican and Middle Eastern influences, eating in Chicago is like going on a food safari. From fusion food to American staples, chow down on cheeseburgers, smoked fish and cemitas in this colourful city. For the best places to try these amazing bites, here’s where to eat in Chicago.

All trip prices are in Euros €

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** Based on Ultimate European plus Greek Island Hopping departing 21st July 2026, as of 1 May 2025.

^ Based on Thai Island Hopper West departing 14th December 2026, as of 1 May 2025.

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