Spend An Afternoon At Navy Pier
Chicagos iconic lakefront destination, Navy Pier plays host to renowned restaurants, shopping opportunities, boat tours, and so much more.
The waterfront space was conceived as merely a freight dock, however, its slowly evolved over the last century today, the must-see destination features exhibits, rides, parks, and unbeatable views of the glistening Lake Michigan.
Countless walking tours pass through the area, which also serves as the main cruise departure point. The Explorer Pass gives you access to the attractions at Navy Pier, plus other 25 attractions and activities in Chicago.
See The Holiday Lights
Just outside the city, Lightscape at Chicago Botanic Garden is an immersive experience that allows visitors to explore the botanic garden after dark. Bask in the glow of twinkling lights, with a different installation around every corner of this after-dark walking path.
And in nearby Lisle, Illumination: Tree Lights at the Morton Arboretum is another dazzling outdoor experience. The one-mile paved path winds through the sprawling arboretum and offers views of captivating lighting designs. Afterward, cozy up by the fire to make smores and head to the concessions tent.
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Taste Of Chicago Festival
In mid-July Grant Park puts on the worlds largest food festival.
The Taste of Chicago Festival drives home the full diversity of Chicagos dining options.
Bring an appetite and you can take a culinary trip around the world, discover the creativity of Chicagos contemporary restaurants or renew your love affair with Chicago classics like Italian beef, cheesecake, pizza and hot dogs.
There are pop-up restaurants, a whole armada of streetfood trucks and stands representing Chicagos top eateries.
You can go sample crazy, or see highly skilled chefs doing their thing at live demonstrations.
And as the perfect accompaniment the festival organises live music by famous acts and the best of Chicagos music scene.
In 2018 George Clinton and the Flaming Lips played the Petrillo Music Shell.
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Order A Slice At Vito & Nicks Pizzeria
Contrary to Chicagos deep-dish pizza reputation, Vito & Nicks Pizzeria has been dishing up Cracker Thin Crust Pizza since the 1950s, and theyve yet put a foot wrong.
A visit to this adored eaterie and youll feel like youve stepped back in time into an old-world Chicago dive restaurant.
This isnt luxury nor sophistication, its just darn good pizza.
Attend The Last Speakeasy
To celebrate the anniversary of the repeal of the prohibition, the Chicago History Museum hosts The Last Speakeasy in December. At this exclusive, adults-only event, guests can enjoy dancing, games, and various types of liquid luck throughout the night while also touring the museum exhibits. Be sure to come dressed to impress! You might just win the 1920s costume contest.
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Get Your Kicks From Magic Tricks At Chicago Magic Lounge
Yeah, we know that magic shows dont really have the coolest reputation but hear us out on this one. The Chicago Magic Lounge is a pretty funky little venue where you might just be spellbound like youre a kid at a birthday party again. Even getting inside this place is like some sort of trick or inside joke as guests enter through what appears to be an old-school laundromat.
Step through the portal in to this world of magic, and spend your evening enjoying some pretty tasty cocktails whilst being suitably impressed, wowed and confused by what the hell is going on and how these tricksters do it.
Appreciate Jazz At The Green Mill
Known across the city for its eclectic jazz performances and poetry readings, The Green Mill is a Chicago treasure.
Its the oldest jazz club in the U.S., welcoming tourists since way back in 1907.
Celebrities and mobsters alike frequented this prohibition-era speakeasy over the years, and travelers continue to do so to this day.
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Unearth Chicagos Criminal Past
Chicago isnt just famous for its pizza . Its also famous for crime. But before we start getting hate, were talking historic crime. Think the Chicago Mob, Bugs Moran, Frank The Enforcer Nitti, The Lady in Red, The Untouchables, Johnny Torrio, John Dillinger and of course the famous, the notorious, Al Capone.
So for one of the coolest things to do in Chicago, go on your very own stake-out and check out places where all these hoodlums gathered. Search out spots like the Holy Name Cathedral, the Biograph Theatre, and the site of the Valentines Day Massacre in Lincoln Park. Nothing quite like a bit of Prohibition-era gang warfare.
Holiday Flower Show At Lincoln Park Conservatory
Starting at the end of November, the Lincoln Park Conservatory becomes blanketed in a sea of Christmas decor for the annual Holiday Flower Show. From poinsettias to towering trees decorated with twinkling lights, the conservatory is an awe-inspiring holiday destination. This year, the show will feature photographs from the 1940s and 1960s to celebrate past holiday memories. Plus, the winter-long event is free to attend! Who said the best things to do in Chicago during December had to be expensive?
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Fun And Exciting Things To Do In Chicago With Kids
There are so many fun things to do in Chicago with kids it can be hard to decide what to do! Here is our list of things that will be fun for the kids and parents on your visit to Chicago along with where to eat and where to stay.
From the museums on the Chicago Lakefront to a food tour and the Ledge there are a ton of family friendly things to do when you visit the city.
Satisfy Your Palate On A Food Tour
Chicago might be renowned for its deep-dish pizza, but the Windy City actually boasts a number of local delicacies.
Try them all as you loop around the city on foot, devouring Chicago-style hot dogs, dipped Italian beef sandwiches, a classic deep-dish slice, and treats of your choice for tea merchants, confectioners, and bakeries.
These locally-led tours take you off the beaten track and away from the tourist traps and chain restaurants youll be guided exclusively through the doors of beloved and authentic local eateries.
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Spend The Day At Oak Street Beach
Thomas Barrat
Who knew that Chicago had beaches? Well, it does. Being on Lake Michigan, you probably knew it at least has a shoreline, but beaches? So if youre looking for romantic things to do in Chicago, pack up a picnic, your best swimmers, and some blankets and make your way to the surprising slice of sand that is Oak Street Beach.
Fairly long and spacious enough for everyone to find a spot, theres even a biking path along the green park behind the beach. And its backed by an impressive bank of skyscrapers. Pretty cool. Even on a winters day its nice for a romantic stroll together, but we would say that its probably more something to do in Chicago in summer. Dont forget sunscreen!
Make Sightseeing Competitive With A Scavenger Hunt
With limitless attractions scattered across the city, walking around from A to B can get a little repetitive. Why not spice it up a bit with a little extra adventure?
The professionally-orchestrated Scavenger Hunt games combine sightseeing with interactivity, sending players all over the city to solve puzzles and complete tasks, Amazing Race-style.
Sign up for a city-wide adventure, or get specific with a hunt centralized to the Magnificent Mile or the Chicago Zoo.
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Second City Classic Food Tour
Location Provided With Ticket Purchase, ~10-minute drive from Union Station
If you have a lengthy layover and a love of food, this is the perfect Union Station layover activity for you. On Second Citys three-hour foodie tour, youll sample classic Chicago tastes. Walk from the Gold Coast neighborhood to Old Town with a guided tour of the local architecture while sampling mom and pop specialty food items along the way.
Bird Watch On The Jetty
You can spot tons of different species all along the Riverwalk, including ducks, ring-billed and herring gulls, rock pigeons, American robins, European starlings, Peregrine Falcons, and more. The Jetty, a cove featuring a series of piers and floating wetland gardens, is a good spot to start.
Audubon Great Lakes offers a monthly birding walk along the river every first Friday at 8 a.m. from July through October. Meet on the Riverwalk just east of the bridge at State Street and Wacker Drive, and bring your binoculars!
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Cruise Chicagos Emerald Necklace
A scenic drive around the city is never a bad idea, especially now that winter is just around the corner. Yes, you could certainly cruise Lake Shore Driveand by all means, you should. But for a lesser-known option that allows you to see the actual beating heart of the city instead of a few stretches of concrete, head to Chicagos Emerald Necklace, a 26-mile network of interior city streets and wide boulevards. Linking together some of the city’s most grandiose parks like Humboldt, Garfield, Washington, and Jackson parks, this is the way Chicago was meant to be seenwith the added bonus of being excellent quarantine-era therapy.
Milwaukee Scavenger Hunt Adventure
Catch a short flight to Milwaukee, where you can join an exciting and fun scavenger hunt adventure! One of the best ways to explore the city, youll use your surroundings to solve clues and complete challenges.
You can stop and go as you please, and take as much time as you need, admiring and learning about the attractions as you go along. Its a really laid-back trip, and a great experience for couples, friends, and families.
You use your smartphone to play the game and navigate the historic streets of Milwaukee, enjoying its modern and unique culture.
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Visit Chicagos Navy Pier
One of the most well-known attractions in Chicago is the Navy Pier.
It is a highlight of visitors visits to the Lake Michigan shore at any time of year, thanks to Winter Wonderland when its cold out and fireworks in the summer.
Here youll find boat tours , the Chicago Childrens Museum, restaurants, and entertainment.
Find out more about how you can spend a few hours at the pier with our post about things to do at the Navy Pier.
Visit The Chicago Childrens Museum
The Chicago Childrens Museum has a lot of fun, hands-on exhibits that are designed to help kids learn about the world around them.
If youre looking for an activity that will engage the imaginations of your children, this is an excellent museum where they can go on a hunt for dinosaur bones, create art, play in a treehouse, and more.
Best of all, admission is free for children 15 and under on the first Sunday of every month, and they offer late hours every Thursday!
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Booze Cruises On Lake Michigan Aboard Anita Dee Ii
Save Booze Cruises on Lake Michigan aboard Anita Dee II to your collection.
See The Light Show At Buckingham Fountain
Once the sun starts to set, head over to the Clarence Buckingham Memorial Fountain in the center of Grant Park.
Before Cloud Gate came along, this historical landmark was Chicagos most-visited attraction, thanks largely to its mesmerizing nightly light show.
The majestic attraction uses as much as 15,000 gallons of water per minute, and it all illuminates up after dusk.
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Discover The Tallest Buildings In Chicago
The windy city is home to some of the most historic skyscrapers in the world, and there are many different ways to see these landmarks.
Whether youd rather save money with a self-guided tour, or you want to see these incredible buildings from the water on a cruise, there are several great Chicago architecture tours to choose from.
Chicago Air & Water Show
To round the whole thing off, heres another big event that the city lays on for free.
The Chicago Air & Water Show goes back to 1959 and remains the citys second favourite festival, as well as the largest free show of its kind in the United States.
Across a weekend in mid-August more than two million people line Lake Michigan, particularly the North Avenue Beach, for an exhibition of supersonic jets, formation flying, sky-diving and skywriting.
These are normally Army and Air Force groups, like the Golden Knights parachute team and the U.S. Air Force Thunderbirds.
Theres no better time to visit 360 Chicago, the Skydeck or take a cruise on the lake, while shore-side restaurants and bars put on viewing parties, though tickets will sell out months in advance.
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Take An Architecture Cruise On The Chicago River
The architecture in the Windy City is unique, historic, and complex, and theres no better vantage point to admire it all than the waters of the Chicago River.
As you cruise under the citys skyscrapers, youll pass the East Bank Club, the old Post Office Building, the Willis Tower, and plenty more.
Tours typically last an hour and a half, and the guides are notably informative and entertaining.
Explore The Harold Washington Library
One of the nations largest and most impressive libraries is located in downtown Chicago and open until 9 pm.
Be sure to take in the architecture on the outside and inside of the building, as well as the glass roof of the Winter Garden on the 9th floor.
You can also create some art for free in the Maker Lab on the 3rd floor, and there is usually free art exhibits for the adults and storytimes in the Childrens Library.
Info: Harold Washington Library is located at 400 S. State St. Check out www.chipublib.org/locations/34/ for events and visitor info.
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Do You Need Travel Insurance
Dont forget to sort your travel insurance! Weve put together a roundup of Travel Insurance for backpackers check it out here, or if youre low on time, get a quote from World Nomads, our favorite travel insurance provider.
Getting an estimate from World Nomads is simple just click the button or image below, fill out the necessary info, and youre on your way!