Last updated on June 27th, 2023 at 03:09 pm

The cultural hub of the midwest, Chicago is a perfect destination for a weekend getaway. But there is so much to see & do, especially if you visit in the summer. In this post, I’ve got you covered all the Chicago must-see, do & eat

I lived in Chicago for 8 years before moving to the East coast a couple of years ago. Showing visitors my beautiful city had become a norm, so much so that a friend of mine often jokingly called me Chicago’s private tour guide. That was the time before I started this blog. It felt odd not writing a post about a city I know so well, a city I still visit & explore with fond memories. So here’s to my Windy City!

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Must Read: Visiting USA for the first time

How many days do you need to see Chicago?

If you are visiting for the first time I’d recommend at least 4-5 days to see Chicago properly. However, 2-3 days i.e. a weekend or a long weekend could be just about enough time to see all the touristy highlights in downtown. Keep in mind though, you won’t be able to do many activities listed below in that short duration.

Best time to visit Chicago

Hands down summer to early fall i.e. in the months of early May to early November is the best time for sightseeing in Chicago. If you happen to visit during the dreaded winter season, worry not, there are still tons of things to do during Christmas in Chicago.

I must admit that I also really love Chicago during St. Patrick’s Day (mid March) when they dye the river green and the entire city turns into a party town.

Disclaimer: This post contains affiliate links

Where to stay in Chicago

If you are only visiting for a couple of days we would recommend staying in hotels in downtown Chicago to be within walking or a short cab ride distance from most of the attractions. Before making your final selection make sure to read Chicago hotel reviews on Trip Advisor. We always read reviews and see traveler’s photos before any bookings.

Sightseeing in Chicago

Below is a list of the top places to see in Chicago as well as some of my favorite hidden city gems. Click on the map below to get a self-guided route that you can print.

Grant Park

Grant Park is a large urban green space giving a breath of fresh air in downtown Chicago. The park extends from Michigan Ave in the west and expands all the way till Lake Michigan on the east. Some of the places I will talk about below such as Millennium Park, Buckingham Fountain, and Art Institute of Chicago are a part of Grant Park.

Millennium Park

Millennium Park is home to some of Chicago’s iconic structures such as the Bean, Jay Pritzker Pavilion, Crown Fountain (or as I like to call it the “Spitting Fountain). The city of Chicago hosts free cultural shows and events here in the summertime, make sure to stop by for one if possible.

Art Institute of Chicago

Just south of Millennium Park, this museum is definitely a treat for art lovers. The Art Institute’s collection boasts some world-famous paintings. TIP: General Admission is free to all Illinois residents every Thursday evening.

Pro Tip: Dan Kiley Plaza is a small garden right next to the Art Institute on its southern side. It is not very frequently visited by tourists but in my opinion, it is worth a sneak peek. 

Photography Tips: This plaza is a great spot for outdoor pre-wedding or portrait photography.

Buckingham Fountain

One of my most cherished spots of all time in Chicago, it was here that Gaurav popped the question! 🙂 FUN FACT: Buckingham Fountain is one of the largest fountains in the world.

Photography Tip: Go visit the fountain at night when the light comes on. Bring your tripod.

Museum Campus

Museum Campus is in the south loop of downtown, is home to three important Museums in Chicago –

• Shedd Aquarium ($39.95/adult & $29.95/child)
• Adler Planetarium ($34.95/adult & $29.95/child)
• Field Museum ($24/adult & $17/child)

On the other side of Museum Campus is Soldier Field, home of Chicago Bears (American football team for those who don’t know). For those visiting with kids, these museums will keep them highly entertained but you might want to invest in Chicago City Pass to save money on all these museums.

Pro Tip: The lakefront on Solidarity Drive in Museum Campus, especially near Adler Planetarium, gives THE BEST views of the Chicago skyline.

Photography Tip: Sunrise & Sunsets are the best time to photograph from here.

How to get to Museum Campus: There is limited street parking on Solidarity Drive so avoid driving if you can. Walking is another option from Millennium Park but that is a long walk so be prepared. We’d recommend taking a shared ride with Uber or Lyft  OR take the public transport from Michigan Ave. Bus #146 from State Street and Bus #J14 from Michigan Ave will take you to the museum campus.

Willis Tower

Willis Tower once called Sears Tower, is a Chicago landmark, which held the title of the tallest building in the world for 25 years since its construction in 1973. Today it is the16th tallest in the world and 2nd tallest building in the US after One World Trade Center in NYC. The story behind this building’s architecture is a genius. Skydeck is the observation deck on top of Willis tower giving 360-degree views from the top. Another interesting feature of Skydeck is the glass ledges that allow you to see Chicago hundreds of feet below you. 

Magnificent Mile

You will hear the buzzword Magnificent Mile a lot in Chicago, in reality, it is nothing but Michigan Avenue that is north of Chicago River. This area of downtown is known for its high-end shopping experience. Whether it’s the designer shops on Michigan Ave or the mall at Water Tower Place, if you have a shopper’s appetite this is your spot.

However, if I was visiting Chicago in the summertime, I’d prefer to stay outdoor enjoying the city. TIP: There are a ton of amazing restaurants, bars, and pubs around the Magnificient mile especially on Hubbard Street.

Here are a few buildings I admire on N. Michigan Ave (click on the map above) –

• The Wrigley Building
• NBC Tower
• Old Chicago Water Tower: The old Chicago water tower is a historic landmark and one of the few surviving structures the survived Great Chicago Fire of 1871. Pro Tip: Take a peek inside the old water tower (yes you can go inside).
• John Hancock Center: It’s the 8^th tallest building in the US with panoramic views from the top which, in my opinion, is even better than Willis Tower. There is an observation deck on the 94^th floor called 360 Chicago with an entrance fee of $23/adult. A new addition in the recent years to this observatory has been a thrill ride called the TILT where a glass ledge tilts outside the building. 

Pro Tip: Instead of going to the observatory head to the Signature Lounge on the 96th floor for some killer views for zero entrance fee. Sunset is the best time to be here. Ladies, don’t forget to check out the loo here .. you’ll thank me later!

• Fourth Presbyterian Church (Pro Tip): Here’s a hidden gem in the city. Right across the street from John Hancock Tower, on N. Michigan Ave, is the Fourth Presbyterian Church. Stop by to view the gothic church as well as it’s well-manicured courtyard garden. It’s quite popular for local wedding photography.

Oak Street Beach OR North Avenue Beach

With gorgeous water body like Lake Michigan comes the temptation of swimming in it. There are a bunch of manmade beaches along the coast of Lake Michigan. Oak Street and North Avenue Beaches are the closest to downtown Chicago and make for a fun day outing.

And it comes without saying that I am referring to summer months because I don’t want anyone to get hypothermia here. Unless you are interested in the Chicago polar plunge?!

Pro Tip: Chicago Air & Water show takes place on North Ave beach and has great visibility from Oak St. beach as well. This year’s show is on the weekend of August 17- 18, 2019 from 10am to 3pm.

Navy Pier

Navy Pier is a nice place to spend a late summer afternoon and evening. There is a giant Ferris wheel, carousel, children’s museum, Shakespeare’s Theater, and indoor shops & restaurants in Navy Pier. It is also the starting point for architectural boat tours and dinner cruises. 

My favorite spot in the summer here is the Beer Garden at the very end of the pier, where they have live music on weekends. And in the winter you cannot miss the festivities at Navy Pier including the Winter Wonderfest.

Pro Tip: Every Wednesday and Saturday in the summer from May 26^th to September 1^st  there is a free fireworks show at Navy Pier.

How to get to Navy Pier: Parking is very expensive so try to avoid driving to Navy Pier. Taking shared car rides with Uber/Lyft or taking public transportation is the best way to get here. Bus #29 from State St. or Bus #124 from Michigan Ave near Millennium Park will get you to Navy Pier.

Lincoln Park Zoo

Located in Lincoln Park neighborhood on the north side of Chicago, this city zoo is FREE to the public. Lincoln Park organizes zoo lights and holiday markets during Christmas time at the zoo. So swing by if you are visiting in November-December time frame.

Pro Tip: Whether or not you have kids, head to Lincoln Park Zoo for not only it’s wildlife but the incredible views of downtown Chicago from this green oasis in the city.

How to get to the zoo: Bus #151 or Bus #143 from Michigan Ave will get you to Lincoln Park Zoo. There is a parking lot in the zoo compound for $35/day, you can get for cheaper on shared rides such as Lyft and Uber if you want to avoid public transport.

Activities to do in Chicago

Below is a list of some fun activities you can add to your Chicago itinerary –

Biking on lakefront

This had to be one of my favorite summer activity with friends. Rent a bike from Ohio Street Beach or from Navy Pier and bike the lakefront trail all the way till Museum Campus and back. You can either rent for a couple of hours or do a bike tour – there are different kinds of bike tours available. The distance is 2 miles one way. I know it sounds a lot like a workout but it’s so worth it! 

CHICAGO RIVER WALK

Below Wacker Drive lies a city gem – Chicago riverside walkway that stretches all the way till the River meets Lake Michigan. It’s perfect for an evening stroll where you’ll also find a bunch of bars, and steps to sit & relax. 

Pro Tip:  At the end of River Walk right before you cross Lake Shore Drive there are dingy looking stairs. Go on top of the stairs up to the street level to get a stellar view of downtown from the bridge. To get a better idea of this spot, watch MyTicklefeet’s Chicago Instagram highlights.

ARCHITECTURAL BOAT TOUR

If you are visiting Chicago in the summer months then you MUST, and I insist, go on an architectural boat tour. You will really thank me later! You cannot leave Chicago without appreciating it’s architectural excellence, so make an effort to learn about it. This tour is one of the best experiences in Chicago in my opinion and I am not even getting paid for saying this.

The skyline view as you cruise the river is exceptional. If I had to recommend a company based on my personal experience it would be Seadog as they give you a thrilling speedboat ride on the lake before the architectural river tour. You can find and compare the architectural boat tours here. 

Pro Tip: Check Groupon for great prices on your favorite tour company. 

LAKE MICHIGAN DInner BOAT CRUISE

Now if you want to get fancy, like the time we did when celebrating Gaurav’s Birthday a couple of years back, book a dinner boat cruise. There are many cruises that depart from Navy Pier, we went with Odyssey and she was a classy experience. You can compare different Dinner Boat Cruises in Chicago here.

CHICAGO RIVER KAYAKING

Finally gave this a try after spending years watching people kayak on the river. It was a unique experience, something we had not done in the city before. Honestly though, if you are doing the architectural tour (which you must!) I would say skip kayaking and the boat cruise. Compare different Chicago kayak tours here. 

ROOFTOP BARS

Wondering why this even made to an activity? Well not only do they have killer views of downtown but many of these rooftops belong to heritage buildings. What better than grabbing a drink on a rooftop (alcoholic or not) to cool down in summer and getting access to historic buildings. We have listed our favorite rooftops in Chicago with amazing views in another post if you are interested in reading. Pro Tip: This one is for the photographers, you are not allowed to take your tripod on these rooftop bars.

COMEDY SHOWS

It might be a lesser known fact but Chicago is popular for its comedy acts. I loved visiting Second City Chicago for some terrific performances. There is also UP Comedy Club, The Annoyance Theater & Bar, and Flat Iron Comedy which is a pop-up comedy venue in Wicker Park.

SPORTS

I cannot talk about Chicago without mentioning sports. Chi-town is home to some legendary teams – Bulls (Basketball), Cubs (Baseball), White Sox (Baseball), Bears (American Football), and Blackhawks (Ice hockey). Perhaps go watch a game while you are in town!

SHOPPING

Although this is usually the last thing on my agenda when traveling, many of you have requested us to include shopping in our posts so here it is. The two streets in downtown Chicago that you should head to for shopping are, Magnificent Mile (I talked about it above) and State Street (between Jackson St. & Randolph St.). However, since this post is from a locals point of view I’d also tell you to check out the quirky shopping neighborhoods like Wicker Park and Pilsen district. 

Best Places to Eat in Chicago

• Big Star – Located in Wicker Park, their chicken tacos are my favorite. They have a vegetarian dish called walking tacos, go figure!
• Kristoff’s Bakery – A hole in the wall, my personal favorite. Their Vanilla Tres Leches with chocolate frosting is the world’s best Tres Leches in my opinion. See our Instagram Chicago stories to get an idea.
• Cafe Ba Ba Reeba – Spanish Tapas restaurant in Lincoln Park, a great place for food and even better for Sangria.
• Artopolis – This cafe in Greektown is my go-to place for delicious Tiramisu. A really nice place to grab a cup of coffee and try their bakery, there is an amazing variety of Greek desserts here.
• Davanti  Enoteca – Small portion shared Italian food in Chicago’s Little Italy.
• 3 Arts Club Café – A fancy place for brunch in Gold Coast. The restaurant is set up in the courtyard of Restoration Hardware which is a unique home goods store to experience as well.
• Bongo Room – is another favorite for American brunch.
• Ras Dashen – One of my favorite place for really good Ethiopian food. It’s located in Edgewater which a bit north of downtown so will need a cab ride to get here.
• Lou Malnati’s Pizzeria – I mean you are in Chicago, how can you leave without trying their famous deep dish pizza. I prefer Lou Malnati’s to any other touristy deep dish place. But to be honest, I am a thin crust pizza person .. No judging! 😉

Phew, this turned out to be a novel! But I really hope that all this inside information helps you plan an amazing trip to Chicago 🙂 Don’t hesitate to ask any questions you might have in the comments below.

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Happy Travelling!