Real Itineraries: 4 Days in Chicago

Real Itineraries: 4 Days in Chicago

Welcome to “Real Itineraries.” In this series, I’ll break down trips I’ve been on, share what I did in real time with honesty and give tips for how you can travel with even better results. In this edition, it’s fun things to do in Chicago! 

In June 2014, I went to Chicago for four days with my friend Beth to run a half marathon for Team Challenge for Crohn’s and Colitis. When we weren’t running, we were ticking off every Chicago recommendation we could. Here’s our Chicago itinerary.


Where we stayed: Hilton Chicago, Michigan Avenue. Team Challenge always puts us up somewhere nice. Our room was clean and comfy with two bathrooms! If you or anyone you know has IBD, you know that this is a real blessing.

How we got around: On foot and by taxi. Chicago is a great taxi town, at least in the city center. We were able to hail taxis near all the sights. Mostly, we walked everywhere we wanted to go since our hotel was in such a great location.

As soon as we dropped our bags, we went out walking. After seven hours of driving we were ready to stretch! We easily ticked off two items on our list: pizza and a tower with a view. Our Chicago itinerary was working out beautifully already!

Giordano’s Pizza: Giordano’s was the most-recommended pizza place to try by our Chicago-loving friends and it did not disappoint. We sat outside at the Gold Coast/Magnificent Mile location near the Hancock Tower. It takes about 45 minutes for a deep-dish pizza to bake, so we ordered a bruschetta appetizer to share. The bruschetta was perfect: light and flavorful with a drizzle of balsamic vinegar over so many tomatoes on toast. It took us awhile to eat and left us with plenty of room for pizza. We chose the extra cheese pizza and it oozed warm melty mozzarella with every slice we pulled from the pie.

Hancock Tower: After dinner, we made for the Signature Room at the Hancock Tower for a drink and to watch the sunset. We didn’t have to wait for a seat, but the only ones left were in the center of the bar, far from the windows. We sat there for about fifteen minutes before anyone even came to tell us that they’d be there shortly to take our order. After five more minutes, we could see that sunset was imminent and we were really annoyed with the service so we bolted out the door, down the elevator, and bought tickets for 360 Chicago (the observatory at the top of the tower). We got up there just in time to watch the sunset. It wasn’t crowded at all so we could take our time enjoying the view and were even able to sit by the windows for awhile.


The day before our race was our only full day without a lot of running so we had to make the most of it. We woke without the help of an alarm at five am and since the sun was already up we decided to get going with it.

Millennium Park and The Bean: Because we rose so early, we saw the usually tourist-riddled Bean all alone. This is the ONLY way to see the Bean. We got some grand selfies:


The Hospital: One of our Team Challenge friends was in the hospital with a flare of her Crohn’s, so once it was reasonably late enough we grabbed a taxi to visit her. Though I hope you won’t have to visit, University of Chicago Center for Care and Discovery was a beautiful hospital. We had breakfast at the cafeteria there, which was actually excellent and the best breakfast we had in Chicago. Just look at the view:


Flaco’s Tacos: Okay, this place wasn’t recommended to us by anyone, but with a name like Flaco’s Tacos we couldn’t pass it up for a quick lunch near our hotel. And the chicken tacos were excellent.

Navy Pier: This place was absolutely crawling with tourists and school groups on field trips. It was so crowded we found the whole experience rather frustrating, but the Ferris Wheel made up for it.


Team Meeting and Pasta Party: In the evening, we quit sightseeing to prep for our half marathon. We met up with the Team Challenge National Team to go over logistics the next day and then attended the Inspirational Pasta Party where we heard from teammates with IBD and Team Challenge staff while loading up on carbs. With a planned 4 am wake-up time we did not hit up the Chicago nightlife.


Half marathon: I’ll spare you the details here, but I did PR and it felt awesome.

Post-race pizza: At the race finish, there was a party on the shore of Lake Michigan including deep dish pizza from Lou Malnati’s. It was so good. I never want to eat anything else post-race. The cheesy, crusty goodness was the perfect finish (after resting for about half an hour to get my appetite). Next trip, I’d like to go to Malnati’s.

A nap and a swim: By the time we returned to the hotel we were exhausted so we took a nap and then sat in the hot tub and went for a short swim. Post-race is when I’m most grateful for the nice places Team Challenge always finds us – the pool was so necessary. After we’d rested a bit we managed to get in two more bits of sightseeing on Saturday.

Chicago-Style Hot Dogs: Just a few blocks from the hotel we discovered Devil Dawgs for dinner. They serve the iconic Chicago style hot dog (in a poppy seed bun smothered with tomatoes, mustard, pickles, sport peppers, and celery salt), a variety of other hot dogs (many with cheese), burgers, fries, and milkshakes. This is the place to get your junk food fix in the South Loop.

Willis Tower: Because we can’t get enough of views of Chicago from above and because it seemed like an easy quest for tired legs, we took a taxi to the Willis Tower after dinner. It was far more crowded than the Hancock Tower had been at the same time the night before, but it was still a lot of fun and surely less crowded than it would be mid-afternoon.

NOTE: If you’re not running a half marathon, there are so many things you could do with your day. Our list of things we didn’t get to is enormous. That list includes:

Buckingham Fountain

Lincoln Park Zoo

The Field Museum

And a number of places recommended by @chicagolunch on Instagram


After a quick breakfast, we decided to check one more recommendation off our list before beginning the long drive home.

Molly’s Cupcakes: We could smell Molly’s from halfway down the block, that unmistakable enticing smell of baking sugar. We bought a dozen giant cupcakes to go because we just couldn’t decide between all the wonderful flavors, everything from classic chocolate to peanut butter Nutella to Key Lime pie.


Our only regret was leaving exploration of the Park West neighborhood to the last minute. There were all kinds of things surrounding Molly’s that looked absolutely fabulous. We did stop in one other place…

The Meatloaf Bakery: Essentially cupcakes for dinner, the delights at The Meatloaf Bakery are not your grandmother’s meatloaf. They’re shaped like cupcakes and baked in cupcake pans but are definitely the best meatloaf ever. We tried a traditional meatloaf and a mac and cheese cup (it was vegetarian) that were both awesome. (If I found myself PMSing in Chicago my go-to dinner would be part The Meatloaf Bakery and part Molly’s Cupcakes.)


We loved our trip to Chicago and can’t wait to go back for another long weekend or a more extended visit. Here are the addresses for all the places mentioned above:

Places to Stay

Hilton Chicago, 720 S Michigan Avenue

Places to Eat

Devil Dawgs, multiple locations

Flaco’s Tacos, multiple locations and they deliver

Giordano’s Pizza, multiple locations

Lou Malnati’s, multiple locations and they ship their pizza (My family ordered from them growing up and it was awesome.)

Molly’s Cupcakes, 2536 North Clark Street and they deliver

The Meatloaf Bakery, 2464 North Clark Street, they also have a food truck, deliver, and ship

Things To Do

The Hancock Tower, 875 N Michigan Avenue

University of Chicago Center for Care and Discovery, 5842 S Maryland Avenue

Millennium Park

Navy Pier, 600 E. Grand Avenue

Willis Tower, 233 South Wacker Drive

Michelob Ultra Chicago Spring 13.1 and 10k, starts and ends at The Park at Lakeshore East

Leave a Reply

Your email address will not be published. Required fields are marked *