The SightDOING Guide to Chicago

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Of all the cities in the United States, Chicago is my absolute favorite.  It’s a big city, but there’s a midwestern friendliness that gives the city a comfortable feel.  Navigating public transportation is incredibly easy, prices are reasonable, and you’ll never run out of things to do.  For an interactive trip to Chicago (without skipping the highlights) try these hands-on twists to old favorites.

Top Chicago SightDOING

Make Your Own Deep Dish Pizza

Sculpting the perfect deep dish crust pizzeria uno unique things to do in chicago
Sculpting the perfect deep dish crust

Why simply eat pizza when you could make it yourself? The original Pizzeria Uno’s now offers morning cooking classes for small groups. Not only will you learn the history of deep dish pizza, but you’ll also get the chance to assemble and customize your own Chicago-style pie. I was surprised by a few ingredients (and nothing screams vacation like pizza and beer at 10am!).

Interact With Your Favorite Museum

I am not a museum person, but my husband definitely is, so I try to find ways to spice up our visits. Luckily, two of Chicago’s best museums have awesome interactive tours.

Inside Chicago’s Field Museum

For the Field Museum, join Watson Adventures to solve a murder mystery among natural history exhibits.  If you join in, you won’t get away with skimming the exhibits: you’ll need to inspect displays carefully and draw conclusions to make it through the game — which is similar to an escape room challenge.

>>>>> Read my full review of a Watson Adventures tour from New York City.

Another awesome way to incorporate sightDOING is by joining Museum Hack at the Art Institute of Chicago.  Throughout your visit, you’ll dig deeper than most people and leave with some really cool “did you know?” trivia to share at your next dinner party.  This is NOT a family-friendly tour and is 100% unorthodox and 200% fun.

>>>>> Read my full review of Museum Hack in Washington DC.

Learn Chicago History

things to do in chicago detours historic good times bar history architecture

Chicago has a fascinating history and it would be a shame to visit the city and not hear at least a few stories about what shaped the city into what it is today.  Of course, if you’re on vacation, a lecture or historical walking tour may not be high on your list of things to do.  For a fun way to learn about Chicago, join a pub crawl through the city.  You’ll visit three bars with great stories and learn about prohibition, jazz, theater, vices, and social clubs.  You’ll get drinks and snacks along the way!

Ride a Bike (at Night!)

unique things to do in chicago bike ride at night skyline
The Chicago Skyline, as seen from Museum Campus

Chicago’s best bike tour is held in the evening so you can see Chicago icons lit up at night.  You’ll pedal past city parks, over famous bridges, and to amazing skyline views.  Why I like night better than day: you’ll have a chance to check out the light show at Buckingham Fountain and if you’re there on the right night, you’ll see fireworks from Navy Pier, too!

Go High Above the Magnificent Mile

If you’re only going to go up one observation deck in Chicago, the sightDOING vote goes to 360 Chicago (formerly the Hancock Observatory).  Here’s why: there’s an enclosed moving platform that literally tilts you out over Michigan Avenue from the 94th Floor.  That’s a one-of-a-kind thrill!  You can also plan your visit to coincide with events like yoga classes, painting hours, or dancing with DJs.

Are you planning a lot of Chicago sites?  The CityPASS includes admission to favorites like 360 Chicago, Shedd Aquarium, the Field Museum, and the Art Institute of Chicago — for about half the cost of buying each ticket separately.  The real value, though, is in skipping the lines.  PricelessBuy through my link (at no extra cost) and help support this site.

Classic Chicago Favorites

Take a Wendella Boat Tour things to in chicago wendella boat tour

Whether or not you’ve ever been interested in architecture, the buildings in Chicago are really cool to look at.  It’s one of the few places where the entire city seems to look great together, partially influenced by rebuilding the city after the fire of 1871.  Wendella has a great cruise down the Chicago River and into Lake Michigan so you can see the city from the heart of it as well as the entire skyline while you’re on the lake.

Check out the Night Sky

Of all of Chicago’s museums, the Adler Planetarium surprised me in the best of ways.  The exhibits are well done, with tons of shows to take in.  If you can, time your visit for their once monthly “Adler After Dark” program which is for adults only.  You’ll get the chance to interact with exhibits and pretend you’re a kid again!

Have some extra time in Chicago?  I highly recommend making a side trip (2-3 days is perfect!) up to Milwaukee.  You’ll find tons of unique things to do in Milwaukee, making it an awesome combination.

Photograph the Sights

things to do in chicago bean
Photo by Vincent Ramundo via

Seeing Chicago’s landmarks is a rite of passage. While it’s nice enough to see them, it’s more fun to glide past the Magnificent Mile, Millennium Park, beaches, and more. Hop on a segway and choose a route that includes all the highlights so you can take your photos while exclaiming, “Look, Ma, no hands!”. They’re easier to ride than they look and you can cover more ground than by heading out on foot.

Where to Eat in Chicago


guide to chicago where to eat
Pumpkin Ravioli at Monteverde – I could eat 100 plates

My favorite restaurant in Chicago is Monteverde in the West Loop.  The Italian food here is divine and built for sharing — so you’ll want to bring a friend (or a big appetite).  Since the menu changes, it’s hard to recommend a specific dish…but if you can, I vote for the octopus appetizer and the pumpkin ravioli.  Make a reservation.


portillos hot dog chicago
Portillo’s Hot Dog in Chicago

Here’s the thing: Portillo’s is probably not the “best” at anything, but they’re a solid 90% on everything and that’s good enough for me.  They’ve got awesome Chicago-style hot dogs, pretty darn good Italian beef, and a fun location in River North.  So if you want to try some Chicago classics without chasing out to the suburbs, this is a good bet.

Argo Tea

I have a habit of visiting Chicago in winter (it’s still great, I promise) which means that I live off hot beverages, like the Maté Laté.  Argo Tea is my drink of choice — and they have convenient locations all over.  Download the app to get your first drink free.

Where to Stay in Chicago

theWit Chicago

thewit bathtub view chicago illinois
View from my bathtub. Not kidding.

My absolute favorite hotel in Chicago, theWit, takes things up a notch. The rooms are amazing, the location can’t be beat (for both walking and access to the “L” train and buses), and breakfast at the on-site restaurant is great.  Book direct for free wi-fi and the chance to earn some Hilton HHonors points.

>>>> Read my full review of theWit hotel.

Inn of Chicago

Want a great location and a great value?  Inn of Chicago consistently has rates about 30% less than comparable hotels along with solid reviews.  For someone who wants a good deal without spending hours scouring for deals, this should be your first pick.

Hilton Chicago O’Hare

The perfect airport hotel.  I’ve had great service, lovely rooms, and the location can’t be beat: just walk across the street from the airport to check in (no shuttle needed!).  When you’re ready to head downtown, you can hop on the L train and be in the city within 40 minutes.  Don’t look anywhere else; the Hilton Chicago O’Hare is a great choice.

Need more hotel ideas?  Find 5 unique hotels in Chicago to round out your trip.

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If my guide helped you plan your trip to Chicago, I appreciate if you make your reservations using the links in this post to help support the site.

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