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48 Hours in Chicago: A Weekend Itinerary

Written by Staff Writer

This blog post was updated on May 12, 2020.

There’s just something about Chicago. Whether it’s the amazing architecture that’s weaved into Babel-like skyscrapers or its colorful history of gangsters and blues musicians, the great cuisine that reflects the melting pot of different cultures, or just the great vibe of one of the most exciting cities in the world. There’s just something …

If you find cheap flights to Chicago and find yourself in the Windy City for a weekend, you might be wondering what to do. You might not be able to do it all in this awesome city, but by following this itinerary you might be able to do a lot more than you think.

Ready? Let’s go!

Day 1 in Chicago

Start off your day with a hearty breakfast on North Milwaukee Avenue, at the Bongo Room, where their customizable omelets, breakfast burritos, and red velvet pancakes will give you all the energy you’ll need for the day ahead.

After breakfast, catch a cab towards North Clark Street, where you can embark on a unique Chicago experience – a 2-hour gangster tour by Untouchable Tours. You won’t get to step off the bus, BUT the witty guides dressed up like goons from the 1920s sharing stories about gangsters and their operations in various neighborhoods around town will definitely make it an interesting ride.

Irish black beer shot inside a Chicago pub

After the tour, grab a quick pint of Guinness at The Kerryman Irish Pub (just around the corner from where the tour should end).

If you’re feeling in the mood to get cultured, stop by the Art Institute of Chicago – you can appreciate some classic art from the masters, including works from Picasso.

Find your way to the Willis Tower — a $30 fee will grant you access to the 103rd floor SkyDeck observation boxes, where you can face your fear of heights with an experience that’s more or less like standing on the clouds.

Chicago Style Deep Dish Cheese Pizza with Tomato Sauce

Once your back on solid ground, make your way to Giordano’s located right in the tower and enjoy a signature Chicago meal – deep dish pizza! It might be quite a mouthful to finish so we hope you have a friend to help out!

You can walk off some of your lunch by making your way over to the Field Museum of Chicago – make sure to check out the stuffed exhibit of the two man-eating Tsavo lions (yep, the same ones in the movie The Ghost and the Darkness).

As evening draws near, head to Chinatown, where you can sample some more excellent food and drinks. You can’t go wrong by stopping at MingHin Cuisine for some dim sum and steamed BBQ pork buns accompanied with a few drinks.

Next, head to the Pilsen neighborhood to Skylark, a great bar that serves up great drinks in a dark and intimate setting. If you’re still feeling peckish, don’t forget to try their tater tots – they’re heavenly!

Special Special Pie Thursday! Pie and a #Pilsner, keep the glass! #veltinspilsner

A photo posted by Pleasant House Pub (@phpub) on

After a few drinks, close out the night at another Chicago fave – Pleasant House Pub. This famous joint is known for its unique meat pies. Try their chicken balti Royal Pie, or a variety of other fillings of meats or veggies.

Better hit the sack and get ready for more on day 2 in Chicago!

Day 2 in Chicago

Start your day off by heading to Horizon Café on North Broadway for breakfast. Their spicy chorizo omelet, eggs benedict, and other breakfast staples are sure to satisfy.

Wrigley Field Marquee

Walk over to the iconic Wrigley Field – home of the Chicago Cubs, where you should get a few great pics outside the “Friendly Confines”.

Spend some time walking around the Wrigleyville neighborhood. You can take a self-guided tour of Graceland Cemetary, where many prominent Chicagoans are buried. The cemetery also has many amazing mausoleums and a beautiful garden.

Make sure you stop by Murphy’s Bleachers, a gruff, legendary sports bar that has some pretty cool baseball memorabilia. You can have a few beers while being literally a stone’s throw away from the stadium.


Image via Flickr – CC BY-SA 2.0 – Jax House

Make your way by cab or train to Millennium Park. Find your way to the Cloud Gate sculpture (known popularly as “the bean”) and click a quick selfie.

While lots of tourists will head to the Shedd Aquarium, we suggest you hit the Adler Planetarium instead, where a $12 adult ticket will give you access to great exhibits about the universe, including amazing IMAX-style theater shows.

Put an egg on it #eggsridehorseback : @_plate

A photo posted by Au Cheval (@auchevalchicago) on

Break for lunch at Au Cheval – a burger joint that showcases its creations in a stylish yet affordable setting.

They say laughter is the best medicine, so get your dose at The Second City, one of Chicago’s most famous comedy clubs that has been the stage for comic stars both new and old.


Go to Buckingham Fountain, one of the largest fountains in the world. Make sure you catch the light and music show that takes place regularly throughout the day (shows take place from around April 11 to November 1 – check the dates before you go so you’re not disappointed).

After you’ve had your funny bone tickled, head across to Wells on Wells, a neighborhood bar that has a great selection of brews and an outside patio that’s great respite from the busy street.

What better way to round out your night than by tasting a Chicago hotdog at Gene & Jude’s? Their usual sweet relish, onions, and beef hotdog that’s covered in french fries is one Chicago experience you’ll savor for a long time to come.

And there you have it — a whirlwind 48 hours in the Windy City!

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