10 Ways To Make The Most Out Of Your Weekend in Chicago

Two weeks ago, Mike and I traveled to Chicago for a long weekend adventure.  Aside from a 5 hour layover last year at Midway when we took the L into the city to eat deep dish pizza, this was both of our first experiences in Chicago.  Looking at the map, we were so overwhelmed by its size.  Where do we stay?  Do we need a car?  What do we do?  Luckily, we have a few friends who live in Charleston now who grew up in Chicago as well as more who recently traveled there.  They gave us some great ideas, and with a little exploring on our own, we think we made the most of our 3 days in the Windy City.  You can also click here to check out the Top 10 Photo Spots we also found in Chicago!  Here's how we spent our weekend:

1. Stay downtown and get a CTA pass: Looking south to the White Sox's stadium and north to Wrigleyville is a huge area (everywhere we knew we'd be going).  We went with a hotel right in the middle, on the Chicago River, Club Quarters.  Billed as a travelers' hotel, the rooms were compact and cozy with our queen-size bed taking up most of the room.  Even the building is small (middle building in the photo below), but the views of the city were great, and it was so perfect for us.  Being walking location to almost everything, we opted not to spend money renting a car (and $50 per day valet parking it), so we got a 3-day CTA pass.  We used the pass so much, and it's definitely the way to go to get all over the city.

2. Start each day with coffee and donuts: And preferably at different places.  There are so many awesome little coffee shops all over the city, like Intellegentsia and Pickwick, but even better were the doughnuts.  We tried Doughnut Vault (twice) and Stan's.

3. Take an Architecture Cruise: Our friends went to Chicago last summer, and this was #1 on their list for us.  We loved not only learning about the city as a whole, but also getting our bearings to see where so many points of interest were in the city.  I'd suggest this on day one of your trip, if you can.  We caught our boat from the Chicago Architecture Foundation, right outside our hotel, but there are tons of options all along that area.

4. Selfie with Cloud Gate: The bean!  This was my #1 for the trip.  It was so perfect, and we had fun taking photos around every side and inside it.  All of Millennium Park is fantastic and really fun to walk around.

5. Climb the Willis Tower: I have to admit, it was scarier than I thought to step out onto The Ledge of the Skydeck.  1,353 feet in the air is no joke!  They had a great exhibit about the history and construction of the building, and it was great to do after we learned the basics on the architecture tour.

6. Rent a Bike: Chicago has an awesome bike share program, and while I was a little too nervous to ride through the narrow city streets, we took advantage all along the waterfront where they had some great bike paths.  We picked up our bikes near Millennium Park, rode up on the Lakefront Trail to North Avenue Beach and back down to the Navy Pier.

7. Grab a beer: Chicago definitely has a wide range of breweries, and we chose to go to two: Goose Island, a more recognized, national brewery, and Revolution, an awesome neighborhood brewpub in Logan Square.

8. Stroll through the Wabash Arts Corridor: Murals are my absolute favorite, and that bubblegum moose just stole my heart!  I could have walked around, sightseeing in this area of the South Loop all day.

9. Eat Italian Food and Chicago Deep Dish: We're tourists, so, of course, we had to go all-out with deep dish.  The last time we stopped in Chicago, we had Lou Malnati's, so this time we went for Giordano's.  I definitely vote for Giordano's!  We also had a delicious Italian meal right before we left the city at Labriola's.  Omg those fried ravioli "nachos" were amazing!

10. Watch sports: The reason we chose this weekend in September to travel to Chicago was because it was the one weekend of the season that the White Sox and Cubs were both in town.  It was the last stop of our summer of baseball, and what a perfect place to finish it off!  Wrigley is (obviously) amazing, and Guaranteed Rate Field was actually really cool, too.  Plus, we got tickets for $5 each for the White Sox.

I, honestly, feel like we accomplished so many of my goals for sightseeing while we were there, and three days in Chicago was a great start.  We definitely want to go back (maybe for St. Patrick's Day!) and go on another one of Chicago Architecture Foundation's tours, climb to the top of the Hancock Center, and visit the Lincoln Park Conservatory.