The best Chicago weekend

Congratulations, you’ve booked a trip to visit The Windy City. This itinerary is perfect for a quick weekend trip to Chi-town: arrive Friday after work, and be on your way home Sunday in the early afternoon.

You’ve arrived! If you want a quick way to get into the city and avoid traffic, take the CTA. It’s one way from O’Hare, and you can purchase a paper ticket or use your mobile wallet.

First stop: pizza. You can’t go to Chicago and not get a deep dish pizza.

Chicago Pizza and Oven Grinder Company is one of a kind. It’s the only location in the city. Get the pizza pot pie, you won’t regret it. The building has some fascinating history… if only these walls could talk. The original brownstone was near the St. Valentine’s Day massacre in 1929 and saw flames in 1971 where all but its frame survived.

The next morning starts with a uniquely Chicago bus tour: a Crime Tour about Gangsters, Mobsters and Criminals. Enjoy the AC and views as you drive around town learning some history of the city that has been swept under the rug.

We did the 10am tour and were done by noon. It was a fun way to learn about the gangs of Chicago and I walked away knowing a lot more history than when I started. I was also very entertained.

Next, grab a light lunch before your next tour.

Mister J’s has a few locations around the city, but do yourself a favor and get a Chicago style hot dog - it comes loaded with relish, mustard, tomatoes, pickles and peppers.

Next up: tour #2. Arrive early for your 1pm Architecture boat tour with Wendella so you can pick your seat. We did a tour that covers architecture on the river and goes out to Lake Michigan.

The boat has a bar so you can start happy hour early as you marvel at the incredible architecture, born out of the tragic Chicago Fire of 1871.

Next, grab another light lunch and some drinks along the River Walk.

Beat Kitchen on the River Walk has water front views, tons of drink options and excellent late afternoon snacks. (The personal pizza and guacamole with chips was excellent and fresh). That will fill up the rest of your afternoon, and its almost time to get ready for dinner.

You’re going to want to make this reservation in advance, but Aba is hands down my favorite meal of 2021.

The ambiance of plants and twinkly lights are nice, but the food is incredible. Its a Mediterranean menu, and you can’t go wrong with the whipped feta, kebabs, avocado falafal or short rib hummus. But really, make a reservation in advance - it fills up fast.

End your night on the 96th floor of the John Hancock building.

This lounge has 360 views of Chicago - you can see the water and a stunning skyscape. There is also a restaurant on the 95th floor, but there’s nothing I like more than a drink with a view.

Before your weekend comes to a close, get brunch at Meli’s cafe in Printer’s Row.

This breakfast and lunch spot has fast service, fresh juice options and a Schitt’s Creek Tropical Cafe vibe. I was shocked at how affordable this spot was, and highly recommend it for brunch before you head back to the airport.

Did you know… the water in Chicago has a green tint because of algae. It really is this color!