Chicago has the food, the history, the architecture, the nightlife, the parks, the family activities, the sports…the list goes on. There’s SO much to do here, which is why I had to create this shortlist for a 48 hour visit for first timers or hard-core lovers (like my husband 😂).

A Guide to Chicago for First Timers

How to get to Chicago

If you’re flying into Chicago O’Hare International Airport (ORD) you can easily get downtown two ways. An uber will take about 50 minutes and cost between $35-50 during most hours but if you call during a surge you’re looking at up to $140 including some Chicago traffic on your commute. You can always take the L Train for an easy 55-minute ride all the way downtown without any transfers for $2.50. Traveler’s choice, but we made the game-time decision of an uber.

You can also fly to Midway (MDW) which is much smaller and less busy than O’Hare. It’s also about 5 miles closer to downtown, so you’ll save a few dollars and minutes commuting the 20ish minutes downtown. If it makes sense from your departure city, this is a great option!

Where to Stay in Chicago

Check in to the lovely luxurious London House Chicago with the best rooftop in Chicago, a Kavanagh favorite. It’s a central location in the middle of it all with incredible views of the river and bridges. Hotel room views mean even more to us these days, as we have a baby with a 7:00 bedtime. We watched the most beautiful sunset over the Chicago bridges right from our hotel room bed. Win!

Speaking of, whenever you travel with a baby (especially to a city) I cannot recommend Babyquip enough. We’ve now rented a crib In Chicago, NYC, Bend Oregon, and Maui. Babyquip is a staple and a lifesaver on The Road Les and Nora Traveled.

What to do in Chicago

• Grab a drink on the LondonHouse rooftop for the best views of the city
• Take a stroll along the Riverwalk
• City Winery Riverwalk at the west loop is where you wanna be.
• Hit Ohio Street Beach. Bring a bathing suit for your little one or a change of clothes… Nora started in a dress and ended in her birthday suit.
• So. many. sports. Chicago is home to the Chicago Cubs, Chicago White Sox (MLB), Chicago Bears (NFL), Chicago Bulls (NBA), Chicago Sky (WNBA), Chicago Blackhawks (NHL) Chicago Fire FC and Chicago Red Stars (NWSL). See who’s playing where and be sure to catch a game!
• See a comedy show at Second City. Learn from our mistakes and buy your tickets ahead of time.
• Visit the (free!) Lincoln Park Zoo
• Take the Chicago architecture river tour. Alex is a trained builder and carpenter so when he raved about it, I knew it would be good but my gosh… it is THE tour you have to take. I can’t wait to take it again and again.
• Visit the Navy Pier and the Bean (of course!)

Where to Eat in Chicago

• Pequod’s for deep-dish pizza… because you have to.
• The above might be fighting words for lovers of Lou Malnati’s Pizzeria. I’m just a visitor and pizza lover so count me in for both pies okay?
• Green City Farmers Market in Lincoln Park and the west loop for brekkie
• Daisies for the lunch and market 11-2 Wednesday – Sunday.
• Lula cafe is an all-day cafe with fresh pastries and a beloved breakfast burrito. The dinner menu looks divine.

It really is such a fun place to be! I even spent time in the windy city during the polar vortex a few years ago and I still adore it. If that’s not true love, I don’t know what is. It’s safe to say, we’ll be back again and again. What do we have to add to our list for the next Chicago stopover?