A Weekend in Chicago


I’m fortunate that my work takes me to my favorite city every fall – Chicago! This year, my trip fell just before my birthday, which I promptly used as a bargaining chip with my husband to convince him that he should come with me for the weekend so I could introduce him to some of my favorite places.

This is a true 48-hour itinerary – we flew in from Boston at 7am on Saturday morning and he caught an early flight back to Boston early Monday. Chicago is a great place to spend a weekend, and you can find direct flights there from nearly anywhere!


AM Coffee and cute sleeves compliments of the W City Center – a wonderful place to stay

If you’re looking for a fun way to spend 48 hours in Chicago, here is how we decided to spend our weekend:

Day 1

  • Start your morning off right with your morning coffee and a stroll through Millennium Park
  • Make your way to Navy Pier (admire the vastness of Lake Michigan)
  • Walk the Chicago Lakefront Trail for 2 miles to Oak Street Beach
  • Gold Coast walking tour – guess which one was Hugh Hefner’s old pad
  • Old Town walking tour – for some window shopping
  • Tour the Lincoln Park Zoo until it closes, then make your way over to Clark Street for dinner

Day 2

  • Another morning coffee and stroll in Grant Park (be sure to watch the fountain go off!)
  • Make your way to city center and identify skyscrapers with the Loop walking tour
  • Magnificent Mile walking tour – and the perfect place to get some Garrett’s Popcorn!
  • Architectural River Cruise through the city
  • Spend the rest of the afternoon at the Art Institute of Chicago
  • End the day with the famous deep dish Chicago pizza

Below I’ve outlined some of the highlights of our trip:chicago1   

Millennium Park

Millennium Park is where the famous “Bean” sculpture sits. Go early and take a few obligatory selfies, then move on – it’s always crowded, so the earlier you can get there the better. Millennium Park is home to many other amusing sites – temporary art installations, Chicago Fashion Week (while we were there), the gorgeous Pavilion by Frank Gehry (may you be lucky enough to stumble upon it when orchestra is warming up).

chicago5chicago9   Buckingham Fountain in Grant Park – located just past the Art Institute of Chicagochicago10


The Art Institute of Chicago

The Art Institute of Chicago is one of my favorite art museums. Unfortunately most of the modern wing (my favorite) was closed for renovations. But there is still so many other beautiful sites to see. Don’t miss the Chagall Window, the popular American Gothic, or Seurat’s famous A Sunday Afternoon on the Island of La Grande Jatte. (I’m currently reading this book, so it made my visit even more interesting). The Art Institute is $25 to get in – and, in my opinion totally worth it! It’s a fantastic art museum.



Navy Pier

Navy Pier is Chicago’s biggest tourist attraction, and in my humble opinion, totally overrated. It’s fun to walk down to see what all the fuss is about, but unless you’re interested in chain restaurants, there’s not much to see. (There is a free Stained Glass Museum, which I would have enjoyed popping into, but we decided to take advantage of the sunshine and stay outside.) To me the best part about the pier is the view of Lake Michigan from the end – it’s hard to believe it’s not the ocean!


Chicago Lakefront Trail

One of my favorite things about Chicago as a city is the extensive amount of parks along the lakefront, and the trails. There is 18 miles of trail Chicagoans have access to right from the city center. We walked along the trail for about two miles while we made our way up to Oak Street Beach – which marks the beginning of the Gold Coast Neighborhood.



The Gold Coast

The Gold Coast is a historic neighborhood that boasts wealthy historical homes. Bonus points if you go in the fall – and see the front steps all decked out for Halloween! We used this free self-guided walking tour to see the highlights.

From there we walked to Old Town – which I had never been to before. We used this free, self-guided walking tour – but I’m not exactly sure what we were supposed to see. While it certainly seems like a nice place for locals to meander on a Saturday morning, it didn’t add a lot of value to our visit other than the fact that it was on our way to the Lincoln Park Zoo.

Lincoln Park Zoo

The Lincoln Park Zoo is one of the largest, free zoos in the world! You feel quite far away from the bustling city, and there are a lot of indoor and outdoor areas to visit. We didn’t get to see the new Baby Rhino, but the gorillas kept us entertained for a while!




Chicago Architectural River Cruise:

I’ve heard good things about the river cruises from a lot of different people. Normally it’s probably not something we would spring for, but at the recommendation of many – we did it and had a great time! There are a number of companies all offering boat tours at several times throughout the day. Most range in price between $25-$45/ticket for a tour in the 60-90 minute range. We ended up taking a tour with Wendella Boats at $28/pp for a 75 minute tour. The tour covers the history of the city of Chicago, as well as dissecting the architecture of the skyline and the historical background of many of the buildings.



I did a bit of hotel hopping on this trip, but all three places I stayed were great, well-located, and I’d recommend staying at any of them:

  1. The W City Center – Right downtown and an easy walking distance within everything.  I’ve never had a bad experience at any W Hotel. Free coffee in the beautiful lobby.
  2. Aloft Chicago O’Hare Hotel – Glorified hipster heaven hotel. (They even have Cornhole and outdoor campfires!) This was my first time at an Aloft hotel and I’d stay there again. It’s perfect if you need to be close to the airport, and their breakfast selection is extensive. It’s not free, but SPG members get a free $5 coupon (which more than covered my coffee and egg and sausage on a croissant).
  3. The Drake – It’s famous for a reason, and it’s beautiful. Another great downtown location that puts you in easy walking distance to any destination.

As for food… well, I think this post has gotten long enough! I’ll be back later this week with Chicago Eats!

What’s your favorite thing to do in Chicago? I’m always looking for suggestions : )

PS – How can it possibly be November!?!?