Our Chicago City Guide

We are counting down our final days here in Chicago, so I thought I would share a Chicago City Guide to share all of our favorite can’t-miss spots. Although we have loved it here, it is time to fly back home to the nest and be back home with family. If the pandemic has taught us anything, it’s that family is ultra important to us. Being so far away from family that we were unable to see them for almost two years is unacceptable in our book. Chicago is still our second home and it’s just so bittersweet to have to say goodbye to the place that has seen us grow and change over the last four years. This city guide is like a love letter to our special Chicago home.

While we are not Chicago natives (I am from Florida, and my husband is from Georgia), we have lived here for over four years. By now, we are pretty familiar with the cool and can’t-miss attractions in Chicago. Most of our Chicago City Guide picks are lesser-known spots on the South Side because that’s where we have been living. The South Side needs some more love! So if you’re coming up to the Windy City to visit or to move, here is a list of places you should definitely check out.

Chicago City Guide – Quintessential Chicago

These are places you’ll find in most city guides that you should definitely check out before you leave

• Cloudgate 
  • If you miss taking a picture at the “bean”, did you even come to Chicago?
• Chicago Riverwalk
  • Fun area with lots of restaurants and ample opportunities for people watching
• Navy Pier Ferris Wheel
  • Ride the Ferris wheel and see the summer fireworks go off
• Architecture Boat Tour (Wendella is good)
  • Pick one that fits your schedule and your budget. Both of the major boat tour companies are excellent. If you’re going in the springtime or early Fall, bring a jacket just in case.
• Willis Tower
  • Get the city pass to take advantage of all the cool spots, including this one, for a discount. Take a picture in the glass enclosure on the top floor if you’re not scared of heights.

• Ride on the “L”
  • For an enjoyable experience, don’t go during morning or afternoon rush hours. For your safety, I wouldn’t ride late at night, either.
• Beatnik
  • There are innumerable amazing restaurants in Chicago, but this one is just so unique and you can eat outside by the river, too!
• Bud Billiken Parade
  • This is on the south side around late August right before school starts back
• The Original Pancake House
  • There are several locations around the country, but this is a great little breakfast spot right by Magnificent Mile if you wanted to grab a bite before you go shopping
• Portillo’s
  • Check out this famous Chicago hot dog joint, and order the hot dogs. My husband did not care for the Italian Beef sandwiches here. For good Italian Beef, go to Al’s on Taylor Street in Little Italy.
• Water Tower shops
  • This is a cool shopping mall that doesn’t look like one from the outside. 
• Magnificent Mile
  • Bring your wallet and go shopping! There are all kinds of stores. It is basically a mall with stores lining the sides of the streets. There is an excellent Christmas Parade that goes through here in December.

Chicago City Guide – On the Southside and Suburbs

• White Sox Game
  • White Sox tickets are really cheap, and the fireworks go off on certain nights when the Sox win. If you don’t want to miss a Cubs game either, check out the cross-town classic where the two teams play each other at Wrigley and Guaranteed Rate fields.
• The Duck Inn
  • This is a Bib Gourmand Michelin Guide restaurant in the Bridgeport neighborhood. It’s an unassuming local spot with outdoor seating in the summertime. Don’t miss their whole roasted duck and their duck hot dogs.

• Lay out on 31st Street Beach
  • This beach can get crowded on holiday weekends, but this is a nice sized beach where you can bring the kiddos and dip your toes in Lake Michigan.
• Museum of Science and Industry
  • This museum is on the south side near the University of Chicago campus. They have lots of special events throughout the year as well that happen after hours for a different kind of museum experience.
• Nana/Ajo/Taco E
  • This is a local Bridgeport spot as well. I was looking for some good Cuban food in Chicago, because I’m from Miami, and I was starting to miss it. For Cuban and Puerto Rican food, Nana is great for brunch and fancier dinners, and Ajo is great for a quick bite. I love the bowls at Ajo! There is a lot of food for the price and they all hit the spot. Taco E has more of the Mexican dishes you would expect, like Tacos and Burritos. All three of these restaurants are owned by the same people. Definitely give these a try!
• Osaka Japanese Gardens
  • These are beautiful gardens located in Jackson Park on the South Side.
• Vienna Beef Hot Dogs
  • This is a Chicago hot dog brand, and there is a little restaurant on Morgan and Pershing that serves these dogs Chicago style.

• Antique Taco
  • There is a location in the Logan Square area, but we went to the one on Morgan and 35th street, which was walking distance from our house. All of the tacos are delicious. Order a horchata for some refreshment and enjoy it on the outdoor patio. This is also a local cop hang out, so the food must be pretty good.
• Brookfield Zoo
  • This is a really nice zoo in the suburbs, but it can get expensive if you are planning on taking the whole family. Check out the free options below if you want to stick to a budget.
• Pancho Pistolas
  • This Mexican restaurant is on 31st street. We go here every year for Cinco de Mayo. The prices are reasonable and their food is delicious. I highly recommend the Al Pastor tacos.
• Phil’s Pizza
  • This is a local, cash-only tavern style pizza shop that has been in the Bridgeport neighborhood for decades. This place is special to us because it is where we went to celebrate the day we got engaged.

• Naperville Riverwalk
  • This is a little ways out in the suburbs, but highly recommended for shopping, dining and an enjoyable outdoor experience.

• Lao Sze Chuan
  • If you really like spicy Chinese food, go here! There are so many menu options, and they serve more authentic Chinese food. If you’re looking for your run-of-the-mill fried rice and General Tso’s, look elsewhere! Check out more of the amazing dining options in Chinatown if you have the chance.
• Bridgeport Coffee
  • This is on 31st and Morgan. The coffee is good, but stay for the ambiance and people watching. There is a huge room in the back where students like to study after class ends, and sidewalk seating during the summer months.

• Greek Prime
  • This is a new spot that just opened up last month. We love the food, and the prices are very reasonable. You don’t have to go all the way to Greektown for good Greek food. This one is on 35th street between Halsted and Morgan.
• County Line Orchard (Hobart, Indiana)
  • If you happen to be in the Chicago area around Late August-Early October, take the drive over to Northwest Indiana and visit County Line Orchard for hayrides, apple picking, and all of the apple cider donuts you could want.
• Peach’s on 47th Street
  • This is our favorite brunch spot! They specialize in soul food and their peach coffee is very good as well. Support a Black-owned business and visit this one!
• Maria’s Packaged Goods
  • This is a hipster spot owned by Ed Marszewski on 31st and Morgan in Bridgeport, right next to Bridgeport Coffee House. There are a lot of community events held here, otherwise enjoy the bar and the delicious food!

• Marz Brewing Co.
  • Bridgeport’s local brewing company has delicious food and all kinds of fun beers to try. It’s definitely a neighborhood gem
• Chicago Botanic Gardens
  • I would budget an entire day to really enjoy these gardens and get your money’s worth
• Morton Arboretum
  • We never got the chance to go here, but it is absolutely gorgeous in the autumn season when the leaves have changed

Chicago City Guide – Budget Friendly (Free)

• Palmisano Park
  • This is a local Bridgeport park, part of the Chicago Parks system. There is a giant hill you can climb up and see wonderful views of the Chicago skyline. There are also running trails and a lake to enjoy here.

• Lincoln Park Zoo
  • This zoo is absolutely free and open to the public. Take the kids and wander around all day, and go as often as you like! 

• Garfield Park Conservatory
  • This is also free, but you can give a donation to help support the Conservatory. There are greenhouse rooms and outdoor exhibits to explore. We are partial to this place because this is where my husband Mark proposed to me in 2017. It is also right off of the Green line if you want to take the “L”.

• Any local neighborhood farmer’s market
  • I can’t guarantee the actual food prices will be affordable, but the experience of walking around and seeing what vendors have to offer is usually free
• Summer Fireworks – Free views from Palmisano Park
  • This is a double-plug for Palmisano Park. You can go down to Navy Pier with all of that traffic and pay for parking to see the fireworks on the 4th of July or on New Year’s Eve, or you can set up your picnic blanket on the hill at Palmisano Park and see fireworks in all directions for free. I personally prefer the latter. We were able to sit and chat with our neighbors and have a great time.

Use this Guide When You Visit Chicago

If you’re planning your visit to Chicago, check out our Chicago City Guide recommendations! They will not disappoint. I put together some classic can’t-miss attractions as well as some of our lesser-known local favorites so that you can enjoy Chicago like a true local. And if you’re planning on moving to the area, I have some tips on finding an apartment that you can check out as well!

Are you planning to visit Chicago sometime soon? Let me know in the comments!