Ideally we’d have plenty of time in every city we visit to explore all the wonderful things that it has to offer. However, sometimes that’s just not possible. When you’re lucky enough to have a few hours in a new city, you take advantage of every second. So when we booked our recent trip back home to Wisconsin, we decided to fly in and out of Chicago so we could spend some time there on the way back. We arrived in Chicago on a Sunday evening and left the next day in the early afternoon. In the meantime, I think we got in a lot of adventure. Here are my suggestions for your quick layover in Chicago.
Where to Stay
Somewhere near the Magnificent Mile. I found a great deal at the Fairfield Inn & Suites on East Ontario Street. It was the perfect location for us, we were able to walk to almost everything we did shown below. We took one Uber during the whole trip. One thing to note for all hotels: If you have a car, figure in the price of parking as well, as it’s quite expensive to park in downtown Chicago! The Fairfield has a free breakfast, which was something we considered when finding a good price.
See the Chicago River (especially if you visit over St. Patrick’s Day)
Make sure you take a walk over the Chicago River. Personally, I think the best views of the river come from the bridge on Michigan Ave., but there are plenty to choose from (photo above, Michigan Ave., photo below, N. Wabash Ave.). However, you can easily knock out two birds with one stone by using the Michigan Ave. bridge so you can stroll down Michigan Ave. as well. Lots of shopping and fun people watching.
This is Chicago’s version of Central Park, although total judgement here: I think Grant Park is much better than Central Park. They’ve spent quite a lot of time/money renovating this park in recent years, and the results are stunning. From winding bridges to rock walls for kids, you’ll definitely be able to spend a lot of time here. You will also find The Bean and Buckingham Fountain here.
It needs no introduction. Hope for a cool sky day to get neat photos. And then try to take just one. It’s like popping a can of Pringles. You can’t have just one. Here’s a task: See if you can get less than 50 other people in your photo. Good luck.
Chicago Deep Dish Pizza
You can’t visit Chicago without eating some deep dish. I did my research beforehand to find the “go-to” pizza palace. My parents used to live in Chicago, so because I respect my elders, I took their advice and went to Gino’s East. That, and I know they know great food. If I had more time, I’d have no problem taste-testing all the pizza places to find the best one. You know, because I can’t trust everyone, even if they are family. Calories don’t count when you’re on vacation anyway.
Gino’s Pizza was perfect. The restaurant is an experience in itself: the interior is fun and unique, and the pizza was delicious! Be prepared to spend some time at any deep dish place you visit, remember it takes quite a bit longer to cook!
You could spend a whole day at the Pier if you wanted, but you’ve gotta at least take a walk out to the end if you only have a few hours. Especially if you love people watching as much as we do.
I’d also recommend not being pregnant during this walk. From the beer gardens at the end of the pier, to fun bars every few feet, you miss out on a lot. Like the tropical goat at the Billy Goat Tavern. My husband was nice enough to drink it for me while I wiped drool from my mouth.
Personally, I’d keep this one off my list (Go Packers!), but for my husband it was a must-see. And to be honest, it fits very will into the day as it’s located right across from the Field Museum and the Shedd Aquarium. We took an Uber from Navy Pier to Soldier Field, and then walked back towards the city. We stopped to take photos in front of the Shedd, but didn’t have enough time to explore inside. If you have more time, it’s a must-see as well.
I’d much rather have visited Wrigley Field, but with only a few hours in the city, it was too far out of the way. I’d add that to my list for next time!
Buckingham Fountain (The Married with Children fountain)
Not only is it a famous Chicago landmark, but it’s also beautiful and the perfect photo op. It’s a lot larger in person than you’d expect, and the views behind it are spectacular.
The Billy Goat Tavern
Last, but certainly not least, you MUST stop at the Billy Goat for a cheeseburger. This place got it’s celebrity from Saturday Night Live’s “Cheeseburger Cheeseburger” skit, but it’s more than just celebrity that make it worth your visit. First of all, it’s located under the city, how cool is that? Second of all, the cheeseburgers are so delicious (and the pickles! oh my!). It’s pretty cheap for a great burger and the experience is a must. Find the steps down to the ‘second city’ on Michigan Ave., directly across the street from the Tribune Tower.
*Don’t have time to find the underground city? You can get a cheeseburger at the Billy Goat at Navy Pier. You just lose the experience of visiting the original.
Overall, there are a million more things to do in Chicago, but we left with satisfaction of a day filled with great experiences.