The Perfect weekend in Chicago
I’ve always wanted to visit Chicago and a earlier this year had the opportunity to visit while attend the HOW DESIGN LIVE conference (for any designers out there it's a conference you shouldn't miss). Since I knew I was going to be busy at the conference during the week, I wasn't going to be able to explore the city. I decided to stay through the weekend so I'd be able to sightsee.
This amazing city is filled with some of the best food, museums & architecture you'll find anywhere. Be ready to be taken by the beauty and awe of this city. Chicago is known as the "windy city" and even on a beautiful sunny day that wind chill can take you by surprise.
One of the best investments you can make for this trip is to purchase the citypass online. This pass gets you into 5 of the top sites in Chicago; saving you money and the opportunity to skip lines. It costs about a $100 and you can use it over a span of no more than 9 days. Seriously best decision I could have made.
The second best investment is to purchase the Hop-On-Hop-Off bus pass. I find that one of the biggest challenges I face when traveling is what’s the easiest, most cost effective way to explore a city. Chicago has great public transportation, lots of taxis, ubers but I found that the Hop-On bus was the best way to play tourist for the weekend. It also gave me the opportunity to learn a lot about the city in such a short time. It probably sounds super touristy to most but seriously such a great option to see a city. There are a couple different passes/tickets you can buy such as a one day pass or a two day pass. I just did the one day pass but if I were do it it again I would have just done the two day pass it’s worth the extra money and convenience. You are able to buy them online or they have a few stalls around the city.
FRIDAY (afternoon or evening)
Upon arrival head to your hotel & find a nice dinner spot near by. I stayed in River North which is a super nice and convenient part of Chicago, especially because my conference was located in the Loop District. There are plenty of hotels around the city as well as AirBnBs.
My first night, I was feeling a bit lazy and I didn't feel like going to far away from my hotel so I decided to explore River North. I headed to Sunda to eat, but the place was super busy and there was a long wait. If you do want to try it make a reservation. Instead I walked a block around the corner to eat at Beatrix. I ordered the Halibut with Thai Watermelon Salad and honestly I was a bit skeptical because it isn't something I would normally order. The bartender recommended it and it didn’t disappoint. Honestly it was so delicious. After dinner I checked out this super cute jazz bar called Blue Chicago. The music was fantastic and the atmosphere was amazing.
Get up bright and early (9:00am) to make the most of the day! I stopped in for a quick breakfast inside my hotel which was free. But if you want to grab a quick breakfast outside your hotel or Airbnb check out Firecakes Donuts, Doughnut Vault both located in river north or Do-Right Donuts which is located in the loop near the first stop of the Hop-on Hop-off bus. If you didn’t purchase your hop on hop off bus ticket yet go to Fort Dearborn (stop 1 by the Chicago River) & you’ll see people standing around with signs for you to be able to purchase it there. Otherwise board the bus and start your tour.
The first stop on the Hop-On Hop-Off is Willis Tower to visit the sky deck. It is a world-renowned building and the eighth-tallest building in the world, it remains the tallest building in the Western Hemisphere at 110 stories tall. Once inside head to the city pass line to get your pass and head on up to the top to view the Sky Deck that overlooks the whole city. If you don’t have the city pass be prepared to wait about 90 minutes. The view was seriously stunning and a bit frightening especially if you look down. I spent about 30 minutes up there and headed back down to continue onto the bus to the next couple stops.
Board the bus to Millennium park & the Bean! I couldn’t resist stopping and taking that typical bean picture since it’s such a classic. The park looks absolutely gorgeous you can see a lot of it from the bus but I sadly didn't have time to walk all the way through it.
I then got back onto the bus and headed to the Shedd Aquarium which you’ll need about 2-4 hours since there is a good amount to see. The aquarium is inside a beautiful building and has a great assortment of sea creatures from all over the world.
Hungry after all your morning activities well, get back on the bus to continue to Stop # 10 (Sheraton Grand) (skip the Field Museum & save it for tomorrow). Stop for lunch at The Purple Pig (10 minute walk from the bus stop).
I walked back to stop #10 to head to the Navy Pier. Explore the pier, hop on the ferries wheel & check out the exhibition, Just make sure to keep an eye out on the last time the bus picks up from the pier. So you can catch it to the John Hancock Observatory.
Next stop is the John Hancock Observatory or 360 Chicago building where you can head to the top for another stunning view of the city. Depending what time you get there you can head around to the bar, grab a drink and watch the sunset.
Once you’re done you can take a stroll down North Michigan Ave which is the huge shopping street. Surrounded amunghst gorgeous archetiture buildings and high-end stores.
I went out for drinks with some friends at Trophy Room but there are lots of great bars and blues jazz bars.
Another early-ish morning check out your room and grab a cab to go to Dove Luncheonette for some breakfast which is right across from Urban Belly. I waited about 15-20 mins while I waited I grabbed a coffee at La Colombe which was right across the street. Once inside Dove Luncheonette we shared the pepper & potato hash and I ordered avocado toast and my friend ordered the tamale de pollo ahumado. I loved the avocado toast and the peter & potato hash was delicious!
After breakfast I went to the Field Museum which you need again about 3-5 hours. I spent about 2 & a half hours inside exploring some of the exhibits. It really wasn’t enough time and natural history museums are way more interesting to me than most other museums.
Anyway you can’t leave this museum without checking out the Inside Ancient Egypt. It talks about how the mummification process happens, the history of Egypt, Pharaohs & much more. It is honestly absolutely amazing and they hold the largest collections of mummies found in any U.S. museum. If you’re short on time quickly check out Evolving Planet, the Dinosaur Hall and Cyrus Tang Hall of China. If time permits Underground Adventure was pretty neat and I heard Specimens was a great exhibit as well. Don’t forget to admire Sue the T-Rex.
Catch a ride back on the Hop on Hop off bus at the Field Museum stop & ride the bus all the way back to stop one or get off at stop 10 and walk your way back to the Art institute. Of course if you are worried about time there are plenty of cabs waiting outside the museums. Grab a quick lunch at Cindy’s Restaurant & rooftop Bar for a great view of the bay as well as enjoy some good food and cocktails.
Finally check out The Art Institute of Chicago the final stop of your weekend. I spend about 1-2 hours here but ideally one could spend 2-5 hours inside exploring and viewing all the artwork. Since time might be an issue check out the back of the brochure, you can grab one at the entrance of the museum. It gives you a list of some of the most popular pieces that you shouldn’t leave the museum without seeing. I not only looked at the brochure but I also asked someone who worked there to get a few more tips. My favorite part of the museum isn't really publicize and that’s the Thorne Miniature Rooms located the level LL. Don’t miss it because it is pretty incredible.
After the Museum I headed back to my hotel and grabbed a cab to the airport. There honestly isn’t many good food options inside the airport so if you have time grab some dinner before you leave. I sadly didn’t and just grabbed a salad from the airport.
Anyway hopefully you enjoyed your visit to Chicago! Here are a few other restaurants and links to give you some more tips.
- Freshii — amazing smoothie bowls & healthy snacks if you are in a hurry. Highly recommend.
- Beatrix — Great dinner & brunch options
- Quartino Chicago
- River Roast
- City Winery — great outdoor spot but chilly with the wind
- The Fremont
- Pequods Pizza — great deep dish pizza. One night after my conference I met up with some friends and enjoyed some amazing deep dish pizza!
Here are some additional links that could be useful to adjust and plan your trip to Chicago.