Here’s your stop by stop guide to visiting Chicago

How wonderful it was to be blessed with great weather in the windy city! Although it was a little bit all over the place from sunny to stormy, cloudy to clear – Chi-town definitely delivered the perfect weekend trip. Chicago is an incredibly accessible city, which makes for a perfect jam-packed itinerary in a few short days.

Getting Around

The Ventra card– definitely invest in a ventra card or the local transportation ticket. A day pass will do you justice if you plan on venturing (get it? Ventra? Venture?)  The card can be used for the L-train and the local bus transit system. Make sure to download the local transit map off of Google Maps – it will make life much easier!

Divy Bikes– Another really great way to get around is biking – you’ll find plenty of Divy bikes, the local bike sharing program! They are very affordable a mere $3 per trip or you can rent the bike for the day for just $15 and can drop it off and pick up it throughout the city. Here’s a full map of the stations.

What to do in Chicago by Neighborhood

The Magnificent Mile & Downtown

Starting off with downtown and the Magnificent Mile or Chicago’s 5^th  Avenue of a commercial district. Plastered with high-end brands and a glamorous mall, the pedestrian friendly stretch connects the Chicago River all the way to Millennium Park.  Let’s break it down.

The Magnificent Mile is also home to some of the city’s notorious landmarks including the historic Water Tower, the Chicago Theater, and the Skydeck at the Sears Tower! Fun fact, if the line at Skydeck is too long, which it typically is- an easy alternative is the Observation Deck at the Hancock tower.

At the tip of the Magnificent Mile is the DuSable Bridge where you can enjoy an open deck boat tour of the city. There are plenty of tours; we enjoyed the architecture cruise with Wendella Boats. Beneath the bridge is River Walk, which wraps along most of the Chicago River and can be a free substitute for discovering the cityscape.

Further South is where you’ll find Millennium Park where the big bean resides. Although it’s actually named the Cloud Gate, big bean still seems fitting. Getting here early is probably a good bet, it could get very crowded on weekends – especially if there are events.

As you exit the millennium park territory you’ll still be in the park’s greater space – the transition takes you to Grant Park where you’ll spot the Buckingham Fountain!

If you’re up for walking, you can walk 30-40 minutes from Grant Park through a pedestrian/bike route. It’s quite a scenic road, passing along the DuSable Harbor then ending at Navy Pier. The pier is kid-friendly, and has a massive food hall offering takeaway options of Chicago’s best food chains – mostly deep-dish pizza.

Logan Square

Quite the hipster façade with a deeply rooted melting pot of a past. Home to the Chicago Greetings Wall, Logan Square is an up and coming gentrified neighborhood – but worth the visit. A lot of historic buildings have been transformed into boutiques, galleries and game rooms.

Longing for a bite? Stop at Lula’s Café for farm-to-table tapas. The best being the beet bruschetta and the glorious grilled feta skillet. Need a mid-day pick me up? Go to the shabby chic Gaslight Coffee, a coffee roaster and café in the center of town.

Wicker Park

Another industrial chic/gentrified neighborhood with murals and sculptures plastered around town. The controversial 606 pedestrian & bike path cuts through the city and extends for 2.7 miles across the northwest side of Chicago. Fun fact: this elevated path used to be the Bloomingdale train line!

Favorite find?  We stumbled inside The Royal Palms Shuffleboard Club– and what a pleasant surprise it was. We must have spent an hour taking in the décor, atmosphere and hip rooftop. Who knew shuffle boarding was so popular? You don’t have to do just that either, there’s an assortment of games and activities throughout the club for anyone to enjoy. If you’re hungry afterwards, across the road is Small Cheval – a popular hamburger & shakes joint with rustic outdoor seating.

Old Town

One of my favorite strolls in Chicago was hands down the city’s old district. Another magnificent mile of boutiques, plenty of restaurants and a surprisingly significant young crowd.

A fun stop is the warehouse turned pizzeria, Happy Camper or Broken English for Mexican food – at least check out J.C Rivera’s massive mural. 

Where to eat

If you’re in Chicago, locals won’t leave you until you try a deep-dish pizza. & rightfully so, they’re hefty but delicious. Some of the best places to grab this Chicagoan delicacy are Giordano’s, Lou Malnati’s and Gino’s East– their reputation supersedes them and the waiting lines do too.

And of course, second to pizza comes dessert. Garret’s Popcorn has left its mark in Chicago and the hearts of all sweet lovers. You can also grab freshly baked doughnuts at Stan’s Donuts or hit up the Nutella Bar.

Two days isn’t enough to try Chicago’s diverse food scene, but it surely gave us a good taste of what’s out there. Check out Top Chef’s CJ Jacobson restaurant Ēma for amazing Mediterranean tapas, the Hampton Social for an outstanding brunch and nautical vibes, and the famous Batter and Berries or even The Purple Pig for a lavish brunch.

The rooftop options in Chi-town are endless, especially in downtown. Z Bar and London House are great for dressing up and catching the sunset. But an even cooler bar is the Spy Bar. A local secret – underground spy themed bar and restaurant, there’s a code to get in but we’ll keep you guessing and waiting until you get there!  

& there you have it!  A quick guide to getting around Chicago and spending a few busy days! Remember to pack for every season imaginable. For more US travel guides, check out these trips ideas here.