Chicago Itinerary: What to Do in Chicago With Two or More Days

Traveling to a new place can be daunting, let alone to a city that has so much to offer. How do you even try to figure out what attractions to see, where to go, and which are worth skipping? This is especially important when you are going for a short trip and you want to maximize your time. Wasting your time by going to an attraction that is not worth it or worth the wait is a point of frustration for me.

My goal today  is to provide a Chicago itinerary of what attractions to visit on a two or three day trip (or more). Every traveler will have different tastes/interest and likes/dislikes, so not all of these recommendations will be suited for everyone. Also, Chicago is a huge city and there is no way that every attraction, great restaurant, or event could be handled in this one post. This itinerary will focus mainly on the top attractions that we recommend visiting while in Chicago. In the future, we will revisit this great city to hopefully fill in the gaps by providing more information and reviews as far as attractions, events, restaurants, etc.

Whether you are a relaxed traveler or an active tourist, have young kids, teenagers or no kids, we all travel differently. Even at various stages in our own life, we may have times where we are not as quick as we once were. In the past, you may have been able to see six attractions in a day, now you are lucky to see four. The point is you know what will serve you best to make this or any trip the most memorable and enjoyable. We are here to help and give some recommendations from what we have found during our time in Chicago. Even if you are staying longer in Chicago, use this itinerary as a guide to know what to expect.

Two Day Trip

Day 1: Don’t you dare sleep in because we got a lot to do! Day one is going to be about some culture, history and science. Based on your pace and how much you want to see, you can try to do everything OR, pick two to three that really interest you and spend a little more time at each one.

Willis Tower  (particularly the Skydeck) – The tower formerly known as the Sears Tower, the classic Chicago building that is found in almost every Chicago skyline picture. The building is 1,353 feet in the air and has several glass observation ledges that let you stand in this glass box and see all the way down. On a clear day you can see about four states from the observation deck. There is also a small museum that will tell you more about the building if interested. Also, a restaurant on the 99^th floor is available if you go while you’re hungry or want to eat with a view. The Skydeck is open from 9am-10pm (April through Sept) and 10am-8pm (Oct through March).  The longest part of this attraction is just getting up to the skydeck. If you have your Citypass or Fast Pass, it will go much quicker than having to stand in line and buy tickets. There will be a small line to go up, but the tower does a good job of getting people up and down. Once you are up there, it doesn’t take too long to see everything, it just depends on how much time you want to spend. Going back down also can take a while. Plan for 45 minutes to an hour.

• Insider Tip 1: The best time to visit is when it opens or after 5:00 PM when the crowds leave to eat. If you go after 5:00 PM, you should be able to see a nice sunset view of the city. If you go during the late morning, early afternoon, expect to stand in line at least an hour.

Art Institute of Chicago – Recently voted the #1 museum in the nation, it goes without saying that this is some of the best art you will ever find. The walls are adorned with some of the most iconic artists and some of their greatest works. Their European painting selection boasts some of the finest works in the world, that includes major Impressionist, Post Impressionist and Modern works that are amazing. Only in Paris will you find better Impressionist art. Even if you are not an art lover, this is a must! If you are an art lover, you could probably spend all day there. For those who like to study every painting and read every description, set aside at least three hours. For those who are going just to see the major works, it could probably be done in an hour to an hour and a half, maybe a little less. The museum opens daily at 10:30 AM and is open until 5:00 PM. If you do get hungry, the museum offers a couple of options, but beware because they are on the expensive side.

• Insider Tip 2: The line gets backed up early so either plan to be there at least 30 minutes prior to opening or get a City Pass and skip the line. More on the pass later. If you can’t get there early, the other option is to go around 2:00-3:00 PM as the crowd does wind down a bit and people start moving on. It will still be a bit busy inside and tough to see some of the paintings, but not as bad during the earlier peak times.
• Insider Tip 3: If you are an Illinois resident and are in the area, there is free general admission on Thursdays from 5:00-8:00 PM.

Next, take a brief one to two minute walk north on Michigan ave to see the next stop.

Millennium Park– Millennium Park is home to the famous Cloud Gate, aka “The Bean”. One of the biggest attractions in the city, Cloud Gate offers a truly amazing piece of art with the city skyline as a backdrop. While you’re there, you can be a kid and jump in the water that is between the Crown Fountain that reflects the faces of Chicago on a 50 ft tower. During the winter, an ice rink is offered to try your hand at skating. While you are there, sit on the Great Lawn or take in a show at the Pritzker Pavilion.

• Insider Tip 4: If you are in need of a place to get away from the weather or need a cool place to sit, visit one of Chicago’s hidden gems, the Chicago Cultural Center, which is directly across the street. This venue offers two large Tiffany stained glass domes (one is even declared the largest). They offer several different art exhibits that showcase local artists and boasts some wonderful interior architecture and décor. The Cultural Center takes up an entire city block and is frequented by many visitors. Plus, the best thing about it is that it is free!

Take another small stroll south to see our next attraction.

Grant Park – With the lake in view and the Art Institute still nearby, stroll through Grant Park to see the Buckingham Fountain. The beautiful fountain showcases a wonderful water display that shoots the water 150 feet into the air. The initial display is at 9:00 AM and  every hour on the hour running for around 20 minutes. On the southwest side of the park is an amazing piece of artwork called Agora, which is over a hundred, nine foot tall headless torsos made of cast iron.

• Insider Tip 5: After seeing the Agora, continue east in the park toward the south end to see the Christopher Columbus statue.

After taking in the fountain, our next stop is the Museum campus which is home to the Field Museum, Adler Planetarium and the Shedd Aquarium. This is where you will probably need to make a decision. Do you like the sea and aquatic life or do you like astronomy? It is possible to do all three but you would have to be extremely fortunate with the lines and zoom through all the exhibits. You will probably not be that lucky and thus a decision will need to be made. Or, if you have an extra day, come back when you have more time to do the one you did not visit. In order to get here, you can take a nice walk, around 1.2 miles from the Art Institute or take the orange or blue line with a brief walk to get to the museums.

• General Tip: If you are a football fan and in the area, be sure to check out Soldier Field. Tours are offered, but be sure to check their website for an up-to-date schedule.

Field Museum – The Field is known for Sue the T-Rex, which is the largest and most complete T-Rex and is worth the price of admission. My favorite part of the museum is the Ancient Egypt exhibit that has a number of mummies and relics. The Field offers many regular exhibits and a nice traveling exhibit offering. Depending on your mood and energy, you could go through the whole museum in 2-3 hours, but this also depends on the type of museum person you are. There are many exhibits that are offered that don’t particularly interest me or are more for kids so I either don’t go through them or just skim through them. The Field Museum is open from 9:00 AM – 5:00 PMand the last admission is at 4:00 PM daily.

• Insider Tip 6: If for some reason you choose not to visit the museum, just stop by and see the architecture as it is simply fantastic. The Field Museum offers some wonderful views of the city as well.

Adler Planetarium – This is a specialty museum that focuses on all things astronomy. It is very interesting and entertaining and is great for families. With exhibitions featuring the solar system, telescopes, and astronomy in culture, there are a lot of things to do and it is very engaging. When we went, I was thoroughly fascinated by the whole thing and the offering was great. Some say plan to spend three hours here, personally, I think you could get through this in one to two hours. I was quite surprised how much I enjoyed this museum and highly recommend it.

• Insider Tip 7: The Adler offers some of the best views of the lake and the Chicago skyline together. Even if you don’t go to the Planetarium, and you have time, just go out there to see the view as it is phenomenal.

Shedd Aquarium – An amazing 32,000 animals are located here! The lines here can get pretty long so see the tip below. Make sure you check their website as to all that is included with the ticket. The dolphin show is extra as well as some other specialty attractions, but it just depends on what you want to see. We did the general admission and were satisfied with that option. But we went without young children and that can be a determining factor for the extras. Plan to spend one to two hours but depending on how much you decide to do, it could be greater than three.

• Insider Tip 8: Like the other museums, it is best to either use the CityPass or buy your tickets online to avoid the long lines. The lines can get out of control fast, which not only makes it difficult to get in, but seeing the different features can be tough as well.

After a long day, you have so many options. You can grab some food around the museum area or even back near the Art Institute or I would suggest going to the 360 Chicago Building (formerly the Hancock Observatory) located three miles north. In order to get to it, you can walk (3 miles north), take a taxi or hop on a combination of public transportation options including the blue and red lines. The ride can take 30-40 minutes but will be a nice relief for your feet. If pressed for time, choose the taxi.

360 Chicago – Another skyscraper that offers some of the best views in the city. A new attraction called TILT is now being offered which offers visitors a downward facing view from 1,000 feet up. The line gets long but the observatory is open from 9:00 AM-11:00 PM with last entry at 10:30 PM. The observatory was voted one of the best views in America by Travel and Leisure. There is some interactive activities for the kids if they are interested.

• Insider Tip 9: Many Chicagoans will tell you to skip the observatory (and ticket fee) and go to the Signature Room at the 95^th restaurant (on the 95^th floor) instead. They do offer a lounge on the 96^th floor so some people (cheapskates like myself) will tell you go to the lounge, order an overpriced $10 drink and enjoy the beautiful view.

Day 1 is an aggressive schedule and is easily modifiable based on your typical sightseeing pace. If you are a quick tourist or go through museums quickly this will be fine and should fit your typical jaunt. But, if you like to go at a leisurely pace, then you may need to adjust. If you were to adjust, you could hold off the Art Institute, the Cultural Center, Millennium Park, and Grant Park to day 2.

Day 2: Some architecture and shopping.

Architecture Cruise – This is beyond a doubt one of the best activities we have done. The tour is so informative but also very entertaining, you get to see and learn so much about the city, plus you get unique views of the various buildings, including a trip out into the lake to see a tremendous view of the entire city skyline. Our personal recommendation is the First Lady Official Chicago Architecture Foundation. The tour is given by the actual architecture foundation docents that have studied and truly know their material. The tour last about an hour and a half but you will need to show up 30 minutes early to make sure you get a good seat. Depending on the time of year, you may need to bring a light jacket.

• Insider Tip 10: Try to be there first thing when they open as it will not be as crowded and it won’t be blistering hot if you go in the summer.
• For more information on this cruise as well as other cruise options, see the Chicago architecture cruise post.

Tribune Tower/Wrigley Building– Just across the river is the landmark Tribune Tower and the Wrigley Building. You don’t necessarily need to go inside the buildings, but both are great buildings to take some pictures of.

Marina City (also known as the Corn Cob towers)– Take a small walk west for a couple of blocks to see this iconic building. This is the same as the above with worth taking pictures of but since it is a mixed use residential/commercial building, it is not worth going inside. The corn cob towers are the famous towers that were shown in the Steve McQueen movie, “The Hunter” and is featured in the background in several popular movies like The Blues Brothers and Ferris Bueller’s Day Off. You will have plenty of pictures of this building from the architecture cruise, so if you are pressed for time, you can skip this.

Michigan Ave – Head back to Michigan Avenue to enjoy some shopping. Be warned, Michigan Ave, aka the “Magnificent Mile,” is home to many higher end stores to fill all your clothing, shoes, and jewelry needs. This area is a very high traffic area so beware of your possessions and stopping in the middle of the walkway or you will get ran over. Also, make sure you check out the Chicago Water Tower which is the only building to survive the great Chicago fire.

• General Tip 2: Some of the best and greatest restaurants in the city are located within minutes of this street. See below for restaurant recommendations.

Navy Pier – Home to the big ferris wheel and different entertainment options, Navy Pier offers several attractions to fill your time. For me, Navy Pier is ok but is more geared toward the tourist and the younger population. The Chicago Children’s Museum is there as well as a stained glass exhibit, but this area is mainly for the kids. Various boat rides and cruises are offered that will appeal to all ages, including the Seadog “cruise”, which is a speedboat, or the Tall Ship Windy, which also features the occasional pirate cruise, among the many boat offerings.

• Insider Tip 11: Once you have planned the dates of your trip, be sure to check places like Groupon, LivingSocial, and TravelZoo for coupons for these cruises as they frequently offer several options.
• Insider Tip 12: There are several free trolleys to Navy Pier that are offered around the area so check for those before driving or grabbing a taxi.

During your evening, check the area and local events to catch a concert at a local blues bar or a musical that is in town.

If you have three days, here is an additional day itinerary

Day 3:

Lincoln Park Zoo: A truly amazing find. This is a great zoo with so many different animals to see. Best of all it is FREE! Right next door is a conservatory which is also fantastic and worth checking out. Plan to stay around three hours and bring your walking shoes. If you decide to drive you will have to pay for parking which will cost you anywhere between $20-$35. Public transportation is also a good option and will save you some money.

Wrigley Field – If you are able to do this before day 3 because you have tickets to a game, by all means go for it. If it isn’t baseball season or the Cubs are not playing at home, go check out the tour at the legendary Wrigley Field. Whether you are a baseball fan or not, this is a must see for any visit to Chicago. A tour will last about 75-90 minutes and there are several options available depending on how much you are willing to pay. Make sure you check the website to get your tickets before they sell out. The non-game day tours allow you to visit the clubhouses and dugout which is always a bonus. I always recommend trying to see a game if you are able to as it will provide a great sense of history.

• General Tip 3: I highly recommend using the red line to get to here instead of driving as the ballpark is about a block from the station. Also, there are some nice places to eat in the area, so make sure you check what is around you. An Al’s Beef is within a few blocks of the stadium and is a Chicago staple.

Bucktown/Wicker Park/Old Town – These are some of my favorite places that are just outside downtown. Each offers a different and unique feel to them. Bucktown and Wicker Park  offer some great shopping opportunities. Old Town is a cool place to go walk around and stop in a few shops.

• Insider Tip 13: If you are in the Bucktown or Wicker Park area, be sure to go to an Intelligentsia Coffee. They are roasting and creating some of the finest coffees around. Even if you are not a fan of coffee, this is a place to check out.

Chicago Sign – Located at the Chicago Theatre, this is another one of those places you have to take a picture of. If you are able to catch a show here, by all means do that. They offer some of the best musicals and plays in the area.

Additional days – If you are in the city for more than three days, here are a few more recommendations

Morton Arboretum – Located in the western suburb of Lisle, the Arboretum offers some of the best and beautiful sites in the area. There are plenty of things to do for all ages. The photographers will love this as there are so many stunning shots available.

Breweries – (We will cover the area breweries in a future post, but for now…) Chicago is home to some of the best craft breweries in the nation. Many already know about Goose Island (yes, I know they got bought out, but it is still worth checking out), but there are several others that are growing in popularity like Revolution (a personal favorite, check their site for a brewery tour availability), Finch’s, Argus (highly recommend), Haymarket, and Two Brothers (in Warrenville, but worth the trip). If you are up for an adventure, travel to Three Floyds just over the state line in Indiana (about an hour away) for a taste of craft beer paradise (be prepared for a long wait).

Second City – Famous comedy club that features some great comics.

Museum of Science and Industry – Building was part of the World Fair back in 1893. Be sure to check their website for additional tickets needed for certain exhibits. A U505 submarine is one of the special attractions and worth seeing if you are in the area.

Chicago Blackhawks – If you are able to attend a Blackhawks game, you must. The atmosphere is unlike any other you will find in pro sports. The crowd is chanting, cheering, singing, and just completely in to the game. It has a special feel to it all and even though it may be hockey, this is a wonderful experience that you will not regret. You might even turn into a Blackhawks fan.

There are so many other options as well, not to mention all that there is to do in the suburbs.

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Final thoughts:

Public Transportation: If you come from an area where public transportation is not very good or you are not used to it, I understand your fears but this is the best way to go in the city. It is some of the best in the country. The CTA has several different options that will suffice for your trip. If you are taking a trip out to the suburbs, go for the Metra as that will save some headaches.

If you will be visiting several of the bigger attractions like the museums, be sure to check out the Go Chicago Card or the Chicago CityPass card. Both offer discounts to the attractions and allow you to skip the ticket line which is always nice.  The Go Chicago card has three different option based on your preference and what all you want to see, including an all-inclusive (all the attractions you can do and are available in 1-5 day options), an explorer pass (choose 3-5 attractions that you will visit), or the “Build Your Own” (essentially for those who will only visit certain attractions). This can also be downloaded to your phone so there is no more paperwork to carry around. For what it is worth, I would highly recommend one of these two attraction passes as it will greatly help you be more efficient and save you money.

Free Days – If you have an account with Bank of America, they offer a program called “Museums on Us” which generally allows a free general admission to select museums on certain days (including weekends). This is how we visited many of the museums in Chicago. Check their website for more details.

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Restaurants – Yes, I did not mention my favorite subject, food. There are so many wonderful options in and around the Chicago area. Some of the best chefs in the world have their restaurants here, including Rick Bayless, Graham Elliot, Tony Mantuano, Paul Kahan, Grant Achatz, Takashi Yagihashi, and Stephanie Izard among others. Chicago offers several Michelin star restaurant as well as some of the best food dives you will find. Below is a list of some of our favorites and local’s favorites (special thanks to our local food expert, ‘L’, for helping us put this list together). I would encourage you to plan where you eat (some will require reservations weeks in advance!), so when you know you’ll be the River North neighborhood, check out Xoco, The Purple Pig, or Rockit Burger, etc.

For Very, Very Special Occasions:

42 grams

Alinea – modern cuisine by Grant Achatz. Also check Aviary and Next restaurant which won the James Beard Award for best new restaurant in 2012.

Very Special Occasion:

Les Nomades

David Burke’s Primehouse

A Special Occasion:

Boka

Girl and the Goat – By Stephanie Izard.

The Publican – by Paul Kahan.

Spiaggia – By Tony Mantuano.

Celebration:

Nico Osteria – By Paul Kahan.

Balena

GT Fish and Oyster

Hot Chocolate

Mercadito

Sink Swim

Frontera/Topolobampo – By Rick Bayless.

A Night on the Town:

Rockit Bar and Gril

Little Goat Diner – By Stephanie Izard.

Slurping Turtle – By Takashi Yagihashi.

Taco Joint

The Purple Pig – by Jimmy Bannos Jr.

Normal Chicago Out and About:

Xoco – by Rick Bayless. A personal favorite.

Eataly

Franks n’ Dawgs

Shake Shack

Falafill

Honey Butter Fried Chicken

Publican Quality Meats

Wow Bao – a small chain that specializes in serving “Hot Asian Buns” is pretty legit.

Glazed and Infused – Awesome donuts and a personal favorite.

These are just a small sampling of some of the most popular and best restaurants in the city.

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Finally, please check back in the future as we continue to add our reviews to the above places. Most of all, enjoy your trip.