Chicago – Eat, See, Stay, Do

A beautiful summertime city with fantastic food, views, shopping and nightlife.

I recently went to Chicago with a group of girlfriends. We select a different city to visit each year and love trying new places. Of course Chicago isn’t NEW to me, but I must admit as many times as I’ve visited for work, I never really spent much time getting to know this wonderful city.

We had so much fun, and a recap of our trip is below!

My besties and suitemates!

Chicago – Stay

We stayed at the Chicago Athletic Association. We were really happy with our choice for this particular weekend. We had a couple of clusters of a room + a suite that slept 4 in total, 2 on each side. It was a nice setup and gave each group of 4 plenty of space to work with and 2 bathrooms each. It was also really centrally located and perfect for our group – right across the street from The Bean and Millenium Park and a short walk to shops.

All that said, I would not say that I’d stay here necessarily again. It was good for what we needed, but I think if I went back with Mike or a smaller group I’d try somewhere different. While it was nice, the hotel was fairly dark, and it just wasn’t aesthetically my vibe.

We had brunch at The Langham and absolutely loved the interiors – that one is next on my list.

The Chicago Athletic Association
One of the suites
Our awesome gift boxes from Moët Hennessy, waiting in our room! That Whispering Angel rosé went QUICK!

Chicago – See & Do

Our stay was 3 nights and 3 days. We packed it in and tried to see as much as we could. It’s clear from the below we did lots of shopping and lots of eating and drinking! Our favorite shopping and lunch day was in the Gold Coast District. Another big highlight for us was our architectural boat tour – while it was touristy, it was super interesting and we learned so much! You can see all the architecture of the city from the water, and I was floored by how many iconic buildings there are there.

We also got lots of steps in. Considering that our hotel was right across from Millenium Park, exploring there was a lot of fun.

Some of our favorite activities:

  • Restaurant hopping in Fulton Market and The West Loop
  • Shopping in the Gold Coast District
  • Shopping on North Michigan and State Street
  • More shopping in Lincoln Park
  • The Chicago Art Institute
  • Millenium Park – The Bean, Crown Fountain, and the waterfront
  • Chicago Architectural Boat Tour
  • Rooftop views – Brunch with a view at Cindy’s and rooftop views from both Nobu and London House
Views from our table at London House
The best restaurants and scene
Crown Fountain in Millenium Park
The Chicago Riverwalk
Our group on the architectural boat tour
The Bean in Millenium Park
Views from Nobu
Millenium Park amphitheater
The Chicago Art Institute
The Chicago Art Institute
Some of the cool architecture around the city

Chicago – Eat!

We did not hold back on food! We loved the food there and tried many new places.

Our favorite lunch spot was at Tavern on Rush in the Gold Coast District. We sat outside, drank champagne, and people watched. It was perfect!

Our favorite dinner spot was at Aba. It was a mediterranean spot with a dreamy rooftop for outdoor seating but also an equally lovely interior. The food was perfect.

The only subpar experience we had was at Maple & Ash, which was pretty new when we visited and we’d heard amazing things. We thought it was overpriced and the food was just okay.

Our favorite lunch at Tavern on Rush in the Gold Coast district
@ Tavern on Rush
The brunch spot in our hotel – Cindy’s!
The food at Cindy’s was good….
…but the views from Cindy’s were AMAZING! (Note: We also went to Cindy’s at night, which was a totally different experience and also very cool.)
Dinner at Maple & Ash – our least favorite
@ Maple & Ash
Dinner at RPM Italian Kitchen, which we really enjoyed
The 2009 vintage Dom Perignon we had at RPM Italian – it was a treat!
More food from RPM Italian Kitchen
Our group at Aba, which was our favorite dinner spot
Food @ Aba
Rooftop @ Aba
The Langham Hotel, where we had brunch at Travelle
@ The Langham
@ The Langham (can you tell I was obsessed with their interiors?)
@ Travelle @ The Langham

Overall & Tips

I would definitely recommend Chicago for an action-packed city trip and August was the perfect time to visit. It felt like New York, but cleaner and easier to get around. Next time, I’d try to work in a comedy show at night but otherwise, I thought our itinerary was pretty repeatable. I was so thankful for the white sneakers I brought because we talked a TON! Those were the real MVPs of the trip!

My tip: wear comfy shoes!

Hope everyone has a great rest of their week!

0 comments on “Chicago – Eat, See, Stay, Do

Replies (Would love to hear your thoughts!)