Our Itinerary for a Weekend Trip to Chicago Trip

Bart and I recently had our 19th anniversary and we celebrated with a quick trip to Chicago.

We picked Chicago because we were pretty sure the weather would be lovely in the middle of September plus there were very inexpensive direct flights

We’d both been to Chicago before – Bart lived there for a summer internship before I met him, my family went a lot when we lived in Wisconsin and then when we’d go back to visit my grandparents, and we went together in 2005 and 2014.

So there wasn’t a lot of pressure to squeeze everything in. We mostly just wanted to relax, eat some great meals, and explore the city.

Here’s what we did on our Chicago trip:

Chicago Trip

Thursday:

• We caught an afternoon flight and landed around 7 p.m. It was BUSY and it took us nearly 30 minutes to get an Uber (we probably should have just taken the train into the city).
• We checked into our hotel – we picked the Peninsula Hotel and it was gorgeous. We were delighted with it the whole weekend.
• My friend Jessica, who is a total foodie and lived in Chicago for several years, said The Girl and the Goat was her favorite place but hard to get a reservation for. When I looked a few weeks before our trip, there was one spot available for Thursday night and with the time difference, an 8:45 p.m. dinner didn’t sound too late and it worked perfectly with our flight times.
• We took an Uber from the hotel to the restaurant and had a fantastic dinner. My favorite dish was the halibut with the tomato and peanut salad coming in second.
• We took an Uber back to our hotel and went to bed.

Friday:

• After a late night, we slept in and then we each did a little work before heading to the hotel gym for a workout (I did an arms video on this app and my arms were sore the rest of the weekend!)
• We came back to the hotel room and got ready for the day and then decided to walk to Au Cheval for lunch. It was about 45 minutes but the weather was beautiful and it was fun to check out the Magnificent Mile and the river.
• Au Cheval doesn’t take reservations so we sat outside for about 25 minutes until a table was ready. We hadn’t had breakfast so we were pretty hungry and it was DELICIOUS. We split a cheeseburger (and added an egg and bacon on) and also split the kale caesar salad which was terrific. After lunch, we swung by Levain down the street and bought a cookie.
• Afterward, we picked up some bikes from a street stand (they all use the Lyft app) and rode all the way to Navy Pier. I’d very much wanted to do some biking, so this was really fun for me, especially because we got e-bikes which made it very easy. We dropped off the bikes at the pier and then walked around it and sat in the shade enjoying the water view and chatting for a while.

• I pulled out my phone and saw that I’d gotten an email for an open table at Alinea, a restaurant that so many people had raved to us about. It is PRICY and I had a little heartburn about actually pushing purchase (even though I’d been watching for weeks for an open table and missed easily half a dozen tables that booked before I could snag it). Bart said we should go, so I paid and then we canceled our reservation at S.K.Y. for the following evening.
• We walked back to our hotel, stopping at a Walgreens to pick up a few snacks and some bandaids since my shoes were hurting my foot. We changed and then walked down to the river for our scheduled boat tour.

• Everyone had suggested we do an architecture tour led by the Architecture Center and we loved it – lots of interesting info and gorgeous views. I’d booked it on purpose to line up with sunset and it was magical to watch all the buildings start to light up as the sun went down.
• Afterward, we walked a block to The Purple Pig where we had a dinner reservation (it was. HOPPING) and everything was delicious, especially the roasted beets.

• Several people had suggested Firecakes Donuts which is open late, so we walked a few blocks to it and bought a pistachio old fashioned donut and then walked home.
• The donut, unfortunately, was very mediocre (when I mentioned this on Instagram many people said we should do Do-Rite or Stan’s donuts instead but I was not anxious to have more doughnuts so we never tried either). Happily the Levain cookie was FANTASTIC.
• We watched the rest of our episode of Loki and then went to bed.

Saturday

• We got up and went for a run – we’d originally planned to split up so Bart could run faster and further but we ended up staying together the whole time, running several miles along the water and then veering into Lincoln Park. Afterward, we walked through Old Town before meandering back to our hotel to get ready for the day.
• We took the Red Line to the Cubs game and arrived shortly after it had begun (we sprung for more expensive tickets so we could sit in the shade – it was HOT!) and bought some Chicago dogs too, which were delicious.

• We ducked out of the losing game during the 8th inning to miss the crowds and took the train back to our hotel (it was already VERY busy on the train even with the game not over yet).
• At our hotel, we watched the last episode of Loki (so good!) and then changed into swimsuits and went to the pool which had gorgeous views of the city from the 19th floor. We hung out in the hot tub and then I swam a few laps before settling in to read on my Kindle (I blew through the whole first Emma M Lion book which I’d been meaning to read all summer after one million people told me how much they loved it).
• Bart stayed at the pool while I went back to shower and start a puzzle (I brought along this one!). When Bart got back, he changed and then we grabbed an Uber to our dinner at Alinea.

• This was MAGICAL. My sister and her husband had gone several years ago and to get to score a table felt like an anniversary miracle. There were about 8 courses and each one was more interesting, fun, and delicious than the last. I loved every second of it.

• Afterward, Bart suggested we walk home which was about 45 minutes. It was a perfect night for a walk and my shoes, which were new and I was a little worried about being uncomfortable for that much walking, were terrific. My favorite part was walking through Old Town which was all lit up and absolutely gorgeous.

Sunday

• We got up and got ready for the day and Bart called to ask if we could push our checkout to 1:00 p.m. (they said it was no problem).
• It was rainy and we were glad for the umbrellas at the hotel on our walk to church a few blocks away.
• After a lovely meeting, we walked back to the hotel, changed out of church clothes and packed up, dropping our bags with the concierge.
• We walked down across the river and to the Art Institute which was VERY busy on a rainy Sunday and enjoyed about an hour and a half seeing the most famous exhibits.

• Afterward, we walked a few blocks to the central public library (we had planned to stop at the Bean too, but it was pouring so we skipped that). We browsed for a bit and then headed back to the river to eat lunch before catching our flight.
• We had a late lunch at Pizzeria Portofino which was delicious and then we headed back to the hotel to pick up our luggage. We got notice that our flight was delayed so we stayed in the lounge for a bit charging our phones and reading until we caught an Uber to the airport.
• Our flight finally took off and a few hours later, we were home, ready for bed after a fun trip!

If you have any other questions about our Chicago trip, let me know in the comments and I’m happy to help!

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