Chicago is an amazing, vibrant city with so much to explore. If you are looking to see it at a more leisurely pace, I would probably recommend 5 days to really see everything. BUT, I’ve never been one to travel at a very leisurely pace and since you can do Chicago in a long weekend and avoid taking any time off work, I’ve made a 3 day itinerary to exploring Chicago and see all of the greatest the city has to offer!
I traveled to Chicago in March of 2013. That was a pretty long time ago (please forgive me for the grainy iPhone 5 photos I am sharing!), but my research game is really strong, so coupled with my actual trip there, you can be assured this is a great 3 day itinerary!
Best time to go
In my opinion, late spring or early summer is definitely the best time to visit and explore Chicago, however it’s great in any season! Nice weather makes getting around easier, the temperatures are more pleasant, and there are a lot of fun, outdoor festivals to take advantage of! Make sure you plug your travel dates into here to see if there is anything of interest you might want to grab tickets to. Chicago is a great sports city as well, home to the Cubs, Bulls, Blackhawks and White Sox, if you are a fan, catching a home game is a treat! There is also a theatre district, and a great live comedy scene. Sports are what brought me there, to see the Blackhawks during the Toews, Kane, Keith, Sharp, et al era. It was fantastic!
Where to stay
Hostel –
Budget: Budget is a bit hard to find in Chicago hostels, but this choice comes in at $86 CAD per night and is a great place to stay; HI Chicago is located right in the center of it all, walking distance to some of the cities best attractions and food. Most bookings include breakfast and are 4-10 bed dorms. Private rooms are also available.
Bougie: this option hits the bougie choice really for price alone, I wouldn’t choose this one over the HI Chicago for any major reason. Coming in about $146USD per night is the Chicago Parthenon Hostel. This is also in a great area, and houses a bar/restaurant in the same complex. This is a great second option if the HI Chicago is booked. There aren’t that many hostel options in the city.
Hotel –
Budget: This one is definitely on the more affordable side for this city, and it also exudes character. Staypineapple is a super cool hotel that has everything you need and a few things you really want too! Brimming with super cool architecture this hotel is right next to Millennium Park which puts you in walking distance to lots of greats sites and amenities. This one comes in just under $400 CAD per night, which is a pretty reasonable rate in the city for summer especially.
Bougie: Although this is a little outside the Loop area, this is the bougiest best located hotel in the city for people who are, well, not price sensitive at all. That is the St. Regis. Chicago. With water views on two sides and the Riverwalk on your doorstop you will have premium access to the city. As well, if staying in for an evening sounds fun, you will be able to take advantage of a beautiful indoor pool, in house spa. and dine at the two amazing restaurants in the hotel, Miru or Tre Dita. Save those Marriot Bonvoy points as this one comes in at about $1300 CAD per night!
I stayed at the Whitehall Hotel, just off the magnificent mile area of the city, and it was a great hotel in a good location. I have recommended hotels mostly in the Loop neighbourhood, as that is where I would stay if I were going again simply for ease of getting around to everything mentioned. This hotel is a bit north for days 2 & 3. However it was a fantastic stay and if you would prefer to be in this area, I definitely would suggest checking it out.
Getting around
I have made this plan such that walking is totally doable, but if you are feeling tired, need a rest, or have limited mobility, Chicago does have a great transit system. The ‘L’ train services many of the city’s hotspots as well as the airports. The bus system is pretty good too, and public transit is definitely your cheapest option. It’s the only way I got around while I was there, including from O’Hare. If you find yourself out pretty late, or want door to door service, grab an Uber or Lyft. I don’t really recommend renting a car as parking is expensive and sparse. When I rented one I used it to go to the outlet mall in Aurora and driving around was easy, but we didn’t have to find parking!
And now, for my recommended itinerary for 3 fun days in Chicago! Of course, these days can be done in any order, and moved around a bit based on the forecast, but it’s a huge city and exploring Chicago is best in sections so you aren’t walking too much or wasting time getting places.
Day 1: Lincoln Park
I would begin my first day in Chicago by heading North and exploring the Lincoln Park neighbourhood. Start on the water side, and there is a free zoo you can go to, or there is also the Lincoln Park Conservatory to check out. Pro tip; it’s warm in there, so if it’s a cold day pop in and check out the florals until you can feel your fingers again! You can pass by the beach for now, you will come back later.
Wrigleyville
Once you are done in this area, head further north to Wrigleyville. Even if sports are not on the top of your list, seeing Wrigley Field and Wrigleyville is a must. If the Cubs have a home game, I recommend getting some tickets, if not for the love of the game, at least for the love of the history.
Wrigley Field is one of the oldest baseball fields in the National League, second only to Fenway in Boston. It has cool things like a hand turned scoreboard, an iconic marquee, and a real “good ol’ days” feel to it. When you are near the field, check out the residential buildings around it and you will see many with seats on the rooftops! When I was there in the winter, there was an ice skating rink set up just outside that you could rent skates and skate at. If you don’t have the option to get tickets to a game, but you really want to see the park, you can book a tour here.
Wrigleyville is also a great place to eat and grab some drinks. By now in the day you are probably getting pretty hungry, so here are some of my recommendations:
- Smoke Daddy Wrigleyville located at 3636 N Clark St., Chicago, IL 60613; great BBQ and key lime pie!
- Tango Sur located at 3763 N Southport Ave, Chicago, IL 60613; Argentina steakhouse
- Dugout Wrigleyville located at 950 W Addison St, Chicago, IL 60613; if you can, get a place on the rooftop for a beautiful skyline view
the North Shore
After you have soaked up the history and fun in Wrigleyville, head back south and soak up some sun on North Avenue Beach. Unless it’s cold and/or there is no sun. It’s still a great beach for a stroll and picturesque views of Lake Michigan though! This is one of Chicago’s most popular beaches. As a Canadian I would definitely brave the chilly waters, but to many it’s more of a lounging beach than a swimming one! The beach is pretty as a postcard, with amazing views of the city’s skyline. There are lots of snacks and drinks to be had in the area, as well you can rent bikes, a jet ski, a volleyball court, you name it!
Feel free to spend lots of time relaxing here and giving those feet a rest if you’ve been walking. You earned it! The last stop of the day is back a little bit more south, and is the (formerly named) John Hancock Building. This skyscraper is located on Michigan Avenue, right on the part that is known as Chicago’s Magnificent Mile. This is where tons of stores have flagship locations, from Louis Vuitton and Gucci to American Girl and Lego!
Best deep Dish Pizza in Chicago
There are a ton of amazing places to eat here, but if you are in Chicago, I bet you want to have some Deep Dish Pizza! These are the two places I would suggest:
- Gino’s East located at 162 E Superior St, Chicago, IL 60611; this place has become a little “famous” with locations in other parts if Illinois, California and even Singapore! The atmosphere is really funky and fun though, and the pizza is yum!
- Giordano’s located at 730 N Rush St, Chicago, IL 60611; this place also has a lot of locations all over the USA, it is highly rated and cheesy as heck!
Both are fantastic options and will give you a really great taste of a true deep dish!
Enjoy the amazing View
To end the day, take a visit up to the observation deck of the John Hancock Building 875 North Michigan Avenue. This building was apparently renamed in 2018 for some weird legal reason with an insurance company and hasn’t yet had its naming right scooped up again. Anyway, this skyscraper is 100 stories tall and has a 360 degree view of the city from the 94th floor. On a clear day you can see 4 different states! There are also private residences in this building, and was actually where comedian-actor Chris Farley lived, and was tragically found dead in his apartment. I’ve shared a lot of views from here in this post already!
If you time it right, you could watch the sunset from here, and I recommend grabbing a drink at the Signature Lounge Bar on the 96th floor. Or, if you skipped pizza and have the pocketbook for it, the Signature Room restaurant has been highly rated.
Now it’s time to head back to where you are staying and get some rest for another fun day tomorrow!
Day 2: Riverwalk
Today is going to keep you close to the rivers East Side. Start the day at the Lake Street Bridge, this is right where the river splits. This is one end of one of Chicago’s newer attractions, the Riverwalk! This is a 1.25 mile long path that takes you from here to Lake Shore Drive. There are lots of great photo ops along the way, cute cafes, places to grab a bite or a drink, and LOTS of bridges. If you visit during St. Patrick’s Day this is also the section of the river that gets dyed green!
At the beginning of the day if you need your caffeine fix, Blue Bottle Coffee is great, and is just north of the river walk at the start, cross at the Franklin-Orleans Street Bridge before you get going. This didn’t exist when I was there, so I don’t have any photos of the actual Riverwalk, but this is the river.
While meandering along the Riverwalk, when you get to Michigan Ave and the DuSable Bridge, make sure you cross the bridge, or at least look North to catch the Wrigley Building. It’s worth taking a look at, as the building is quite architecturally nice, it was built in the 1920’s. It can be toured, but I don’t think it’s worth the time in this itinerary.
Navy Pier
After a look at the Wrigley building, it doesn’t matter which side of the river you continue on, but make your way to Navy Pier. This will be on the north side, but there is the ability to reach it if you stay on the south side. Navy Pier is home to the Centennial Wheel, which is a big Ferris wheel offering great views of the city. Feel free to take a ride, it’s fun and the view is nice. But, if the line is really long as it tends to be in nicer weather, I would skip it. You will be getting a great view later today as well.
While at Navy Pier, grab some snacks; Chicago style hot dogs or popcorn can both be found here. Depending on your group’s interests, the pier hosts a Shakespeare Theatre, a Children’s Museum, carnival games and is also a great place to catch a boat tour from.
After you’re done at Navy Pier, you’ll want to head further south to Millennium Park which houses one of the most unique things in Chicago; Cloud Gate – also known as ‘The Bean’. You probably know what this is, but if not Cloud Gate is a large stainless steel art sculpture that is well known for how it is able to reflect the city’s skyline. It appears totally seamless and is shaped like, well, a bean! It’s free, but often very busy. Make sure you get some photos here, it’s really very cool!
If you haven’t eaten anything but snacks yet, I’m sure you’re starving. There is a very cool place close to here that I want to recommend to you called Goddess and the Baker located at 33 South Wabash Ave, Chicago, IL 60603; everything here is super ‘instagrammable’ and delicious! There is a ton of great places in this area though, so if you have a certain craving I am sure you can find it!
Art Institute of Chicago
After eating, it’s time to take in some culture at the Art Institute of Chicago. I’m going to come right out and say it; I’m not really a museum person. But sometimes they do have neat guest exhibitions worth checking out. This, dear reader, is going to be up to you to decide how much or how little (or if at all) time you spend inside. This building, like the famous Public Library on 5th Ave in NYC, is flanked by two lions. They often get decorated for big sports events or holidays. They are worth seeing even if you choose to skip the museum itself.
Behind the museum, is Grant Park which is home to Buckingham Fountain. This fountain performs a show on the hour from 9:00am on, and after dusk moves to every 20 minutes. It’s beautiful, but it does not run in colder months, so skip this if you’re visiting then.
Willis Tower
The last stop of your second day ends with yet another skyscraper observation deck and a spectacular view. Head to Willis Tower (formally named Sears Tower) and head up to the Skydeck. This is on the 103rd floor of the building and is most famous for the glass boxes that you can walk out into and see down to the ground. It’s quite funny to watch people with a fear of heights hype themselves up to go into one. It’s a very popular attraction, so I would get tickets in advance if traveling in peak season.
For dinner and the rest of the evening, do what you feel like. This last attraction will leave you well positioned to check out some restaurants on W Randolph Street. Here are some recommendations:
- Girl & The Goat located at 809 W Randolph St, Chicago, IL 60607; highly raved about even now 13 years after it opened
- Au Cheval located at 800 W Randolph St, Chicago, IL 60607; gets the vote for best burger in town
- Kaiser Tiger located at 1415 W Randolph St, Chicago, IL 60607; if it’s cold, they set up a curling rink, how cool is that?
This area is also close to the United Center where the Blackhawks and Bulls play home games, as well as many other great ticketed events take place. If your attending something there, these make great pre-game food spots as well.
If you’re looking for a more party scene, head to the River North area where you will find The Underground Chicago, Howl at the Moon, or Joy District.
For me, if I was heading back I would want to check out Second City, where many big name comedians got their start and see what comedy or improv they were showing. I love nothing more than a good comedy show!
Day 3: A day of inside stuff! Shedd Aquarium, Adler Planetarium, Field Museum and/or Museum of Science and Industry
This is a great plan for a rainy day. All 4 things I am suggesting are indoor activities, and 3 of them are all close together!
One of the biggest highlights of my trip was going to the Adler Planetarium. They have a very cool room where you get a chair that fully reclines and you get to watch an amazing movie like you are gazing up at the stars. I highly recommend a few hours here.
From there, I would go to the Shedd Aquarium, and then the Field Museum. That’s what makes sense logistically. But, if it were me I would skip the aquarium if you only had time for two. AND, I would skip both the aquarium and the museum and head to the Museum of Science and Industry.
I’ll keep today’s notes short. I think you can figure out these things on your own without too much help. All 4 have great websites showing what they have to offer that I have linked above.
Chicago is such a fun and amazing city. I hope found some of these recommendations helpful! Once you’re back, leave me a comment and let me know what your favorite part of the city was. I look forward to hearing from you and your stories about exploring Chicago!
xx Jess
