The Best of Chicago: Where to Eat, Sleep, Run & Explore

The Best of Chicago: Where to Eat, Sleep, Run & Explore

Headsweats Ambassador Jill Monroe is preparing for the Chicago Marathon. If you’ll be there too, check out her advice on the best food, lodging and places to run in the windy city. And don’t forget to visit her blog (Travel.Run.Repeat) for more!

The 2017 Chicago Marathon is rapidly approaching. It’s time to start planning your trip if you haven’t already! Reservations for hotels have hopefully been made, but if not don’t panic! I have some suggestions for you. You should also start thinking about pre-race dinner reservations since the city of Chicago will be crowded with runners from all over the world with the same intention of eating the perfect meal. Don’t be stuck wandering around Chicago trying to find a place that has last minute availabilities for your carb-rich dinner! I wouldn’t want you to accidentally stroll into UNO’s Pizzeria & Grill, a chain restaurant, thinking you’re getting authentic deep dish pizza. Be informed and know what’s best in town!

The Chicago Marathon was my second marathon and first Abbott World Marathon Majors. I had the time of my life running this race. My husband is from the Chicago area, and my in-laws live there as well. I’ve combined my personal suggestions with that of my family and friends to bring you a very detailed and thorough list of places to eat, sleep and play in Chicago! Oh, and of course if you’re just visiting Chicago for business or vacation and need suggestions on places to run, I’ve got you covered!



In order to really experience Chicago, you’ll need to try deep dish pizza. My favorite is Lou Malnati’s. My father-in-saw says “Get the butter crust!” I don’t remember trying the butter crust, but I’ll have to go back just to try it. You probably won’t need more than one or two slices. It is very filling!


Runners love their pre-race pasta meal, so if you’re planning ahead consider La Scarola and make a reservation. You will forget you’re in America when you eat here. This place has some of the best Italian food in the world.


Craving tacos? Or want to try something different? Check out Mercadio’s. Here’s the best way to describe this place:

“Cocktails and upscale Mexican eats keep this popular hangout bustling with a hip, young crowd.”



For creative Chinese fare from a celebrity chef Stephanie Izard, who won Bravo’s Top

Chef, check out Duck Duck Goat. Other restaurants from Chef Izard is Girl & the Goat and Little Goat Diner. All of these are highly recommended! Check out the Little Goat Diner for breakfast.


Craving a burger after your race? For “the best burger in the city” try Au Cheval.


“An homage to oysters, pork and beerThe Publican’s eclectic menu is inspired by simple farmhouse fare in a space evocative of a European beer hall. Chef-Partner Paul Kahan, Executive Chef Cosmo Goss and Chef de Cuisine Jacob Saben have developed a network of purveyors to supply the restaurant with hand-selected and sustainably-raised fish, seafood and pork.” This place was highly recommended by several of my friends.


SHERATON CHICAGOSheraton - Chicago

I love the location of this hotel. It’s located right on the water (pictured to the right). You can access the Lake Shore Trail easily from this spot and you’ll have a great view of the city. There are plenty of restaurants you can walk to or ones within the hotel. They serve Starbucks as well (always a plus for me). You can even walk to a Whole Foods Market. And Michigan Ave is also easy to walk to. Click here for their website.

The following luxury hotels come highly recommended: 


Public Hotels website. This hotel reminds me of something I would see in Tokyo, Japan. It’s clean, refined, sophisticated and totally unique. I love how there are separate sections of each room for “work, sleep & relaxation”. Check it out.


Another gorgeous luxury hotel located in the heart of River North. Check out the Kimpton Hotel Palomar.


This came highly recommended and I was told it was one of the nicest hotels in the world. Judging by the pictures, this 5 star luxury hotel has it all!

“Majestic views of the cityscape, the Chicago River, and Lake Michigan. Legendary hotel hospitality established in 1865. All housed in a skyscraper designed by renowned architect Mies van der Rohe.”


Another gorgeous luxury boutique hotel with a fantastic view and location. Click here for more details.

The following hotels are more reasonably priced and still in a fantastic location: 


I love the look and feel of this hotel, and it’s location is also perfect. The price is reasonable for what you’re getting and it’s location. Click here.


I am a fan of LaQuinta Inn & Suites. This location is great and the rates are fantastic considering you’re staying in the heart of Chicago. Check this one out.



One of my favorite things to do before the Chicago Marathon is to take a tour of Chicago by boat! This is a great way to see the city, but not do a lot of walking. Check out Shoreline Sightseeing, specifically their Chicago Architecture Tour.


Another cool thing to do before or after the marathon is to visit Navy Pier and take a ride on the Ferris Wheel.


Check out the famous Wrigley Field and watch the World Champion Chicago Cubs play baseball. There’s no better way to embrace the essence of Chicago than to watch a baseball game in the heart of the city in this iconic stadium. Try a Chicago hot dog too!


Check out Maggie Daley Park downtown, if you truly want to “play”. Activities here range from mini golf to rock wall climbing, tennis to skating and more! Just a word of caution: Don’t participate in any extreme sports BEFORE your marathon. Save these activities for a day or two after. Or perhaps suggest your family or friends entertain themselves here while you rest or run. Tip: Check out Cindy’s Rooftop Bar in the Chicago Athletic Association.

navy pier chicago.jpg



One of my favorite things about Chicago is Garrett popcorn. Try the Chicago mix. Take home a tin full of popcorn for your family or co-workers!


I am a big iced tea fan. Argo has some of the best iced tea I’ve ever tasted. They have a variety of drinks and cafe food, but I usually go just for the tea.  My favorite is the green tea ginger twist! Cafes are located all over Chicago, including one on Michigan Ave.


If you’re visiting Chicago for the marathon, chances are you won’t want to do a lot of walking. But if you’re there for work and need a place to run, check out these suggestions:

5 Places to Run in Chicago:


The obvious place to run is Lakefront Trail. “An impressive 18-mile-long stretch, Chicago’s Lakefront Trail is a paved path that extends from Ardmore Street (5800 N. Sheridan Road) on the North Side to 71st Street (7100 S. South Shore Drive) on the South Side.” When I was here for business I did my 14 mile long run along this trail. It was perfect!


I hope you enjoy your stay in Chicago! I am very excited to be there for the 2017 Chicago Marathon. Follow me on social media ( for updates on my training and reminders about this race and other Abbott World Marathon Majors. See you in Chicago!

-Jill M.

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