How About a Week in Chicago? What to See, Eat and Explore in the Windy City

How About a Week in Chicago? What to See, Eat and Explore in the Windy City

We spent a week in Chicago on our way back from Europe. Rob had a conference for work and our friend Shane decided to come with us after spending the last week in Croatia. What a nice way to get over jetlag and acclimate to life in the United States!

We had such a fun time thanks to your advice and my Aunt’s recommendations. I wasn’t planning on writing about our time in Chicago, but it was too great to keep secret!  We stayed in a studio apartment, nicely equipped, in the recently converted Randolph Towers building on Randolph and LaSalle St. The staff here were super friendly and the pool on the roof was a daily treat. The weather was ideal in late May and everyone was so nice – between the friendliness of Croatians and the Chicago locals, I think my don’t-talk-to-strangers San Franciscan ways have been permanently reformed.

Things to See and Explore:

  • The Chicago Architecture Foundation’s 90-minute boat tour of the city was very interesting. We sat back with drinks from the bar as skyscraper after skyscraper went by. Be sure to bring a hat and extra sunblock for the ride. 
  • The Art Institute Museum is massive and full of so many nice impressionist paintings. We ran across all kinds of Roman artifacts tied back to places we’d just been in Croatia. The old Chicago Stock Exchange trading room tucked in the back is a hidden gem. 
  • My octogenarian Aunt took us on a locals-view walking tour of The Loop, Millennium Park and State Street. She showed us around Marshall Field’s (now Macy’s) where she was an elevator operator, the old and new public library and the gorgeous Palmer House Hotel. 
  • On Saturday, we rented bikes and rode North along the lake shore. We couldn’t believe that the Conservatory and high-quality Lincoln Park Zoo were both free. Rode south out to Adler Planetarium on our way back. 
  • Everyone loves The Bean for a reason! It must break some kind of record for the number of selfies taken by visitors. 
  • Shane and I took a professional barista class at Intelligentsia Roasting Works out on the West Side. Very informative, the class teaches you how to pull a perfect shot, make latte art and forever judge every barista who serves you coffee. 
  • Drinks at the bar on top of TheWit were a perfect end to a long day of exploring.
  • Shopping on Magnificent Mile is a workout, it seems to keep going forever. 
  • I don’t love heights. Shane had a good time at the top of the Sears (now Willis) Tower Skydeck ledge. Both he and Rob had a good time on top of the Hancock Tower. An extra $5 gets you lowered off the building on the new Tilt feature. 
  • Navy Pier was under construction when we visited with my Aunt, it looks like they have exciting plans for the future. Had a nice snack in the Crystal Garden and walked through the stained glass museum.

Things to Eat:
Chicago was a shock to my system after nine weeks of eating essentially nothing but grilled fish, plain yogurt, olives, dark chocolate and tomatoes. I think I gained 10lbs in a week.

  • Chicago-style deep dish pizza is a must. We ate at Lou Malnati’s downtown, which was pretty good, and at Pequod’s a 30 minute train ride away, which was even better. 
  • On a recommendation from a hilarious and helpful woman at the culture center, we stopped for lunch at The Wiener Circle in Lincoln Park. This little grill place is known for the staff throwing insults and cursing, but everyone was polite and charming to us – go figure. 
  • I love a good sandwich and Potbelly Sandwiches delivered. The chicken salad barely edged out the italian as my favorite. 
  • I was craving Indian food after nine weeks away and we stopped in to Naansense for lunch the very first day. The roti roll “tacos” with lentil croquettes and paneer were amazing. 
  • Had a good brew-pub dinner at The Gage. Fish and chips for me, with pickle chips instead of fries.
  • Stopped in at Do-Rite Donuts at the exact moment my appetite for more Chicago-style fried food gave out. The donuts were good, but not worth the calories. 
  • As advised, I picked up the “Chicago mix” of cheese popcorn and carmel corn from Garrett’s. Too sweet and greasy for my taste, but it smells divine. 
  • Siena Tavern was one of the weirder dining experiences I’ve ever had. The food and wine were SO good but the service was SO bad. It took hours for us to get our entrees. We were a big group, and maybe they had some kind of crisis in the kitchen?  

I’m tired (and hungry) just reading these lists. What a fantastic city!

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There are 6 comments for this article
  1. AEOT at 4:25 pm

    Lived in Chicago for 9 years and Pequods is my FAVORITE!!! We have been gone 5 years now and it's still on our "we miss it so much" list. It's the crust that no one else can duplicate. Yum.

  2. Jenn at 10:01 pm

    Thank you so much for your detailed travel log posts! They must be so fun for you to look back on, and they are fun for me as I plan "future vacations" in my head.

    One request: could you revisit your "what to pack" post and maybe show all the ways you mixed together the items you did pack into different outfits? It would be fun and helpful for those of us with limited ability to do that.

  3. Molly S. at 9:06 pm

    That *was* you! As a longtime reader, I couldn't believe my eyes when I saw you at the Wiener Circle as I was riding by. I convinced myself that it wasn't you, because I thought you were abroad, but it was you! So glad you enjoyed my fantastic city!

  4. mrsem Author at 11:11 pm

    Too funny, Molly! Next time we'll have to meet up 🙂

  5. Carla at 11:44 pm

    Aww, makes me homesick for my hometown! Glad you enjoyed your visit. ps I think the folks at Wiener Circle are mostly rude to slurring drunk yuppies late at night.

  6. Katie at 10:10 pm

    Man, I LOVE Lou Malnatis and crave the Garrett's chicago mix!

    But you missed the Rick Bayless powerhouse of Frontera Grill/Topolobampo/Xoco?!?! For shame. They are spectacular!