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  • Writer's pictureJared Cotta

City Guide: Chicago, Marvel at the American Midwest

Updated: Sep 19, 2020

Chicago is one of America's greatest cities and the undisputed epicenter of the American Midwest. It has been a symbol of innovation, culture, and industry since the early 1900s. Chicago adopted progressive and inclusive laws early in its history which gave rise to a steady flow of immigrants from both the segregated South and Europe.

A massive workforce built Chicago into a city of architectural marvels. The grandiose structures are just one of Chicago's incredible draws. The city also has epic green spaces, fantastic museums, and spectacular waterfronts. Any trip to “The Windy City” should include a visit to Navy Pier and Millennium Park to simply appreciate the beauty of the city.

In our episode we interviewed two of our wonderful friends that are familiar with Chicago. Dan Chang is living in Chicago and working for LinkedIn. He has been friends with the Cotta Brothers for many years and not only does he love the food the city has to offer but also the welcoming environment he has experienced since moving there. Danielle Abel is Brendan's girlfriend and spent 4 months living in the suburbs of Chicago during a Physical Therapy school internship. She explored the city every weekend and was able to find out what were the best spots to visit. Both had a great perspective on Chicago and we are excited to share some of their recommendations here!


Happy Lamb Hot Pot - This unique Mongolian Hot Pot restaurant can be found in Chinatown and is ideal for dinner on a cold Chicago night.

485 Massachusetts Ave, Cambridge, MA 02139

Green Street Smoked Meats - A popular BBQ restaurant near the Fulton River District, this spot is perfect for eating and relaxing after a day of walking around the city.

12 N Green St, Chicago, IL 60607

Jeni’s Ice Cream - Craft ice cream shop that makes for an ideal treat during Chicago’s warmer months. There are several Jeni’s locations around the city, including one right around the corner from Green Street Smoked Meats

908 W Randolph St, Chicago, IL 60607

Girl and the Goat - Opened by Stephanie Izard, one of the most celebrated restauranteurs in Chicago, this West Loop hotspot offers a wide variety of unique and flavorful small plates. Trust us on this one, the hype is real.

809 W Randolph St, Chicago, IL 60607

Duck Duck Goat - Another innovative restaurant from renowned chef and restaurateur Stephanie Izard, this hotspot offers creative dim sum dishes and Chinese classics. The goat dishes are always the winners, of course.

857 W Fulton Market, Chicago, IL 60607

Little Goat Diner - A diner style brunch spot opened by the same celebrity chef behind Girl and the Goat. The menu features classic comfort food dishes as well as some more unique dishes, this is the perfect place to start a day in Chicago.

820 W Randolph St, Chicago, IL 60607

Portillo’s - This Chicago based restaurant chain offers authentic, Chicago style hot dogs and other classic Midwestern dishes. With several locations throughout the city, Portillo’s allows you to have an iconic Windy City meal on the go.

Best Deep Dish Pizza

Lou Malnati’s Pizza - Perfectly prepared deep dish pizza with high quality toppings. With over 50 locations in the greater Chicago area, no matter where you are you won’t have any trouble finding a Lou Malnati’s in order to escape the cold and try a Chicago dining staple.

Pequod’s Pizza - While it may not hold our #1 spot, Pequod’s is still a must hit spot in the city. Known for their “carmelized” crust, Pequod’s offers a deep dish experience like no other


Federales - Located in Chicago’s booming West Loop, this open air tequila bar offers quality Mexican food and cocktails. It’s a must hit during a night out in one of Chicago’s most exciting neighborhoods

180 N Morgan St, Chicago, IL 60607

LondonHouse - Rooftop cocktail bar overlooking the Chicago River located in the LondonHouse hotel. The atmosphere and breathtaking view make it the perfect place to go for a romantic night in the city.

85 E Wacker Dr, Chicago, IL 60601

City Hall (now called Recess) - This political themed bar and restaurant in West Loop is definitely worth visiting for a drink. Check their calendar beforehand, you might be in town for one of their popular trivia nights.

838 W Kinzie St, Chicago, IL 60642

Untitled - Located in downtown Chicago, this prohibition themed supper club and bar offers a huge whiskey selection and live jazz music.

Dan’s Tip: One of the best Old Fashioned’s in the city

111 W Kinzie St, Chicago, IL 60654

Kingston Mines - With bands playing on 2 separate stages, this Lincoln Park Jazz club is a great place to have a drink and take in some of Chicago’s famous live music.

Danielle’s Tip: This place may charge a cover of around $15 so be prepared for that but it’s definitely worth it to experience the live music found within

2548 N Halsted St, Chicago, IL 60614

The Highline - This trendy sports bar located in River North is the ideal place to grab a drink from their extensive drink menu and watch a game in one of the most passionate sports cities in the country.

Danielle’s Tip: This is the meet up spot for the University of Georgia alumni association so any Bulldogs visiting the city should stop by for a UGA game! Go Dawgs!

169 W Kinzie St, Chicago, IL 60654


Architecture tour - Cruise up the scenic Chicago river and maybe even enjoy a drink while you learn about unique structures that surround you and give Chicago one of the most captivating skylines in the country. By far one of the best tours this city has to offer.

Northeast corner of Michigan Ave. and Wacker Dr. Look for the blue awning marking the stairway entrance.

Navy Pier - Don’t let the touristy vibe fool you, this iconic attraction is a must see for anyone seeing the city for the first time. Filled with art, bars, and the world famous Centennial Wheel, there’s a reason Navy Pier is such a popular spot in a city with so much to offer.

600 E Grand Ave, Chicago, IL 60611

Millenium Park - The center of public art and culture in the city of Chicago. Millenium Park is home to such iconic landmarks as the Crown Fountain, BP Pedestrian Bridge, and the famous Chicago Bean. Which is not overrated!

201 E Randolph St, Chicago, IL 60602

Lakeshore Drive - A path running alongside the coastline where Chicago meets Lake Michigan. A popular spot for walking, running, and biking.

Chicago Art Institute - Housed in one of the most magnificent and picturesque buildings in the city, this iconic art museum is home to one of the largest and most impressive collections in the United States.

111 S Michigan Ave, Chicago, IL 60603

The iO Theater - This famous improv theater in Lincoln Park offers a wide variety of shows each night and features some of the most talented comedians in the city.

1501 N Kingsbury St, Chicago, IL 60642

Nature and Excursions:

Cubs Game at Wrigley Field - No trip to Chicago would be complete without a trip to Wrigley Field to watch one of the most beloved teams, in "America's pastime". The Cubs’ avid fan base makes every game exciting and the history found in the park will intrigue even a casual observer of the sport.

1060 W Addison St, Chicago, IL 60613

Morton Arboretum - There’s so much to see in the small towns surrounding Chicago and the Morton Arboretum is the ideal location to take in some nature during a trip outside the city. This gorgeous public park and outdoor museum can be found in the Chicago suburb of Lisle, IL.

4100 IL-53, Lisle, IL 60532

These are the spots that came up during the episode but obviously there are many more, feel free to reach out on the website or through IG DM (@cottabros_travelclub) to tell us your favorite place in this destination.

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