Chicago! This year I was finally able to check the Windy City off of my bucket list. I spent three and a half days exploring the city sometimes by myself and sometimes with a friend. There is a good public transportation system, so I suggest you use it in order to save money. Check out my itinerary for a long weekend in Chicago.
Day 1- Lincoln Park & Old Town
Start your day at the Lincoln Park Zoo. It’s free! I walked in at the start of the sea lion show. I spent a good bit of the morning wandering around seeing all of the different animals. As you exit the zoo near the kangaroos, you will come across a bridge with a great view of the city. From there, you can walk through Lincoln Park toward Lake Michigan.
The weather was hot, so I enjoyed my time ambling along the water and checking out the view of the city and the sailboats. At this point, I was getting hungry. There are a couple of places along the water, but one man informed me that most of them close after Labor Day. They “reopened” that weekend in September because it was so nice out but had a limited menu. In the prime summer time, this would be a good spot to grab a drink and perhaps a small lunch.
Chicago History Museum– From the beach, I walked back into the city. I crossed by the Chicago History Museum at the edge of Lincoln Park. If you are into history, this could be a good place to explore. I did not go in but history buffs would enjoy.
Old Town Chicago
I quickly found myself in Old Town Chicago. It was an enjoyable neighborhood for an afternoon stroll that I would frequent if I lived in Chicago.
North Wells Street- I happened to stumble upon this street in Old Town and immediately liked it. There are lots of cute shops and restaurants. The chocoholic that I am, I made sure to stop by Cocoa + Co and work my way down to The Fudge Pot that displays a variety of chocolate in all different shapes and designs. This would be a good place to grab dinner or drinks from the various restaurants lining the street. The road also features places that stood out to me like The Spice House, Broken English Taco Pub, and the famous Jeni’s Splendid Ice Creams. Personally, I found the iconic ice cream shop to be underwhelming, but the long lines seems to suggest that I am in the minority.
Day 2- Museum Campus, Millennium Park, & Skydeck
Day 2 will be a day of walking and sightseeing. I suggest you wear comfortable shoes today. Depending on what is going on and what you want to do (or not do) at Museum Campus, you may want to reorder this list so that you hit certain areas during the day or at night. You can either begin exploring Museum Campus and work your way north to the city center, or skip the Museum Campus activities and start your day in the heart of the city. If you choose the later, you could then finish with a sunset view of the city on Lake Front Trail.
This area of Chicago features Adler Planetarium, the Shedd Aquarium, and the Field Museum of Natural History. It is also home to Soldier Field, not your average looking stadium. This area alone could take up your whole day if you wanted it to. The architecture is worth viewing at least if you aren’t interested in going inside.
Lake Front Trail-
This path runs along Lake Michigan in both directions well beyond the downtown area of Chicago. Follow this path from Museum Campus into the city and find a great view of Chicago. If you wanted to skip the Museum Campus attractions, you could choose to end your day walking along this path toward that area. After leaving a late afternoon game at Soldier Field, my friend and I watched the sun set on the city from this path.
Buckingham Fountain– If you follow Lake Front Trail into the city, you will stumble upon Buckingham Fountain, one of the largest fountains in the world. It is active from May to October. Every hour on the hour there is a water show accompanied by lights as it gets dark. The final show starts at 10:35 p.m.
Chicago Cultural Center & Millennium Park-
Walk beyond the fountain to Michigan Avenue and continue north on that street. You will come up along Millennium Park on your right and the Chicago Cultural Center to your left. Snap a picture at the famous Bean, but be sure to also check out the rest of Millennium Park including the Jay Pritzer Pavilion. At night there are often events that you can go to, so look at the schedule ahead of time. I happened to be there for a concert to celebrate Mexico’s Independence Day. Stop in to the Chicago Cultural Center while you are there. It is free and features some impressive architecture as well as different art exhibits.
Hungry? Try the Tavern at the Park for dinner. It is across the street from Millennium Park and has a rooftop bar. If you choose to start your day in the city center by the bean instead, go to Wildberry Pancakes & Cafe. My friend, a local, jumped at the prospect of grabbing breakfast there.
Still have more time?
And if you want to see ALL of Chicago, head to the sky with the Skydeck Chicago. I personally hate heights, so I stayed clear of this building, but it is a big tourist spot. (**The Skydeck can be a bit pricey so consider the John Hancock instead described in Day 3.)
Day 3- River, Magnificent Mile, & Navy Pier
After a long day of walking on Day 2, let Day 3 be a bit more relaxing.
Start your morning with a stroll along the Chicago Riverwalk. I enjoy nothing more than walking along the water in cities. While wandering along the riverwalk, my friend and I stumbled upon the McCormick Bridgehouse & Chicago River Museum. Find it on Michigan Avenue. On Sundays it is free. It a small museum but has lots of interesting facts about Chicago and its bridges. You can also peek out of the tower windows. It is definitely worth stopping in on Sunday.
Chicago Architecture Tour- While you are by the river, go for a Chicago architecture tour on a boat. There are a few different companies to choose from, but the tours typically last a little over an hour. While they also tend to be a bit pricey, the tours give you a good history of Chicago and some fun sightseeing. It can be a good way to see Chicago while resting your feet from your long day yesterday.
Once you are done with the boat, head north to the Magnificent Mile. This stretch of city blocks features lots of shopping and dining places. You could spend a whole afternoon on a shopping spree or just walk the street and window shop for a bit.
After you have your fair share of shopping, you can either walk or hop a free trolley to Navy Pier. Navy Pier is a popular tourist spot and for good reason. After all of that walking this weekend, reward yourself with some delicious carbs and yummy calories. You must have a deep dish pizza from Giordano’s and some Garrett popcorn. They are two Chicago food icons. Order your pizza first, and then browse the small shops while you wait for your name to be called. Save room for popcorn and head up to the top of Navy Pier. Check out the greenhouse and rides. There is also another great view of the skyline and Lake Michigan. In the summer Navy Pier does fireworks at night; just check the schedule.
**John Hancock- End your day with a drink on the top floor. Get a great view of the city. Ladies, be sure to visit the bathroom as it boasts the best view of the city the hotel offers.
Day 4 – Bonus Day in Chicago!
If you have more than 3 days in the Windy City or some extra time before a flight, you will be able to do a little more and possibly get outside of the big tourist stops. Some of them are in the same general area of Chicago, so you would be able to hit a few in a couple of hours.
Yolk– Hungry? If you only have time to grab breakfast, Yolk may be a good spot to hit. There are a few restaurants throughout the city.
Wrigley Field– If you are a baseball fan, you can visit Wrigley Field. You have the option to just see it from the outside or sign up for a tour lasting an hour to an hour and a half. The field itself is far away from Downtown so plan ahead for transportation time.
Museum Campus- If you neglected to visit any of the attractions on the other days or have more you wanted to explore. Museum Campus can be a good place to kill a few hours.
Chicago French Market– This is an indoor food market. It says French, but there is food from all different ethnicities. I made the mistake of going here for breakfast. Although there was no crowd, the breakfast options were more limited. Who wants Chinese food and empanadas for breakfast? Definitely make this a lunch stop.
Chicago Gangster Tour– Chicago is home to a rich history of gangsters and mob bosses. There are various tours you can take that showcase these criminal icons. Just do your research to discover which tour is best for you.
Big Monster Toys– This is a little out of the city, but I window shopped on the walk. While I didn’t actually go inside, I did enjoy posing in front of the giant door
Greektown– On my walk back toward the city from Big Monster Toys, I passed through Greektown. You will notice the blue and white street flags. If Greek food tickles your fancy, you can eat here. There is also the National Hellenic Museum (closed on Mondays) if you are interested.
Chinatown- This is an area I didn’t get to in Chicago. I love exploring the cultural areas of every city, but unfortunately, I ran out of time for this one since it is farther south.
La Vaca– Can you say tequila? This restaurant serves tasty tacos and delicious margarita pitchers. They have a large outdoor area and good music. It is a hot spot on Saturday nights, so we grabbed some drinks at the bar while we waited for our table. It rests on a street that is home to a variety of Mexican restaurants and bars if you are looking for a good taco Tuesday spot or just craving a burrito.
Don’t forget; you are in a city! There are always events going on. You just have to seek them out.