As a Midwestern girl, born and raised, it’s no surprise that post-college I ended up here in Chicago. Now, after having lived in this wonderful city for nearly two years, I feel well-equipped to share my knowledge for any travelers passing through or for anyone considering making Chicago their home.
This city has a distinct feel, characterized by a beautiful architectural aesthetic with friendly, down-to-earth people. You’ll never be lacking for things to do, no matter the season, as Chicago is known for its food, sports, nightlife, festivals, restaurants, and museums.
If you’re looking to spend some time in the Windy City, this guide will give you all you need to know.
Neighborhoods
Chicago is made up of many neighborhoods, each with its own character. The city is laid out from south to north, hugging Lake Michigan to the east. This is good to know, because realizing that the lake is always east no matter where you are in the city will help you get your bearings right away.
The best way to explain each of Chicago’s prominent neighborhoods would be to start south and work our way north…
Chicago Lakefront
The South Side
Chicago’s infamous South Side is often recognized for its intense poverty and street violence, but truly it is much more than that. Go visit Hyde Park, The Museum of Science and Industry, and the University of Chicago, or go see a White Sox game, the set where the hit show Shameless was filmed, or the Pilsen and Chinatown neighborhoods, which are nearby.
The Loop
Just north of the South Side is Chicago’s Loop neighborhood, which can be considered the true “downtown” of the City. This is where you’ll find Millennium Park and some of the best shopping and restaurants in Chicago. West of the river is referred to as the West Loop, which is an up-and-coming area known for its chic restaurant and nightlife scene.
Millennium Park
River North
Moving north, you’ll come to the River North neighborhood, named this way because it’s the neighborhood just north of the Chicago River. Here you’ll discover the Magnificent Mile, Water Tower Place shopping mall, and the Chicago Riverwalk, which is especially beautiful at night. River North is also a hub for Chicago nightlife, and this is where you’ll find some of the most iconic nightclubs, bars, and restaurants in the city.
Gold Coast
Chicago’s Gold Coast neighborhood is a wealthy residential neighborhood, as its name would imply, just north of River North. It’s characterized by larger homes and high-rise apartment buildings which offer fantastic views of the lake. This area is known for upscale restaurants and shopping as well.
Boating on Lake Michigan
Old Town
Moving north and a bit west, you’ll come across Chicago’s historic Old Town neighborhood. Old Town is one of my favorites, as its picturesque tree-lined streets are beautiful year round. This is where you’ll find plenty of cute boutiques, restaurants, pubs and bars. Wells Street is Old Town’s main strip, and it’s the heart of the area’s nightlife. Old Town is one of the most popular neighborhoods to live in in the city.
Lincoln Park
Lincoln Park is my absolute favorite neighborhood in Chicago, as it’s the neighborhood that I call home! Lincoln Park houses the Chicago Zoo and plant conservatory, which are both completely free to the public. It’s very close to the lake and is filled with charming cafes, coffee shops, boutiques, and restaurants. Popular with families, Lincoln Park is a relaxed place to live and definitely worth a visit if you’re in the area.
Lincoln Park
Lakeview
Just north of Lincoln Park, you’ll come to Lakeview. Lakeview is one of the more lively and fun neighborhoods in the city, typically attracting a younger crowd. It is also home to Chicago’s Boystown which is especially exciting during the Pride Parade in the summer. This neighborhood has lots of funky restaurants, bars, comedy clubs, and shopping, and if you don’t stop for late night macaroni-stuffed grilled cheese at Cheesie’s, you’re missing out!
Wrigleyville
Continuing north past Lakeview, you’ll come to Wrigleyville, named for the Wrigley stadium which is home to the Chicago Cubs. The neighborhood is mainly characterized by sports bars, nightclubs, and restaurants relating to the team, and is an absolute blast for a night out or during a Cubs game. If you’re looking for cheap hot dogs and beer, this is the place.
My friends and I getting rowdy at a Cubs game!
Logan Square, Bucktown, and Wicker Park
Parallel to the lake-hugging neighborhoods I’ve just mentioned, Chicago’s west side has a several up-and-coming neighborhoods as well. Logan Square, Bucktown, and Wicker Park are all becoming more and more gentrified, which tends to attract a more hipster and artsy crowd. In these neighborhoods, there is no shortage of quirky bookshops, art galleries, speakeasies, and local theaters. In Wicker Park especially, you’ll find some great trendy bars and restaurants, such as Big Star and Paradise Park. All three areas have a variety of patios, craft cocktail and rooftop bars as well.
Lake Michigan in the Winter
Seasons
One of the best and worst things about Chicago is its seasons. Winter can be bone-chillingly cold, as exhibited by the Polar Vortex we’ve experienced this winter, but there is a silver lining. The city has plenty of fun winter activities that will help you forget how absolutely freezing you are! For example, ice skating in Millennium Park or Wrigleyville, drinking hot chocolate (or spiked hot chocolate) in one of the many bars and cafes, and visiting the wintertime Christkindlmarket downtown. It also helps that the city covered in snow is an incredibly beautiful sight.
On the flip side of that, Chicago’s summertime is unlike anything else you have ever, and probably will ever experience. There is a buzz in the air, an excitement, and everyone in the city feels it. When summer comes, we don’t waste a minute of it. From sunbathing at North Avenue Beach to drinking craft cocktails at rooftop bars and patios, watching outdoor movies in the park, going to free outdoor concerts, strolling through farmer’s markets, and of course, attending music festivals such as Lollapalooza and Mamby on the Beach, Chicago is the absolute best place to be during summer.
Summertime Chi!
If you’re a sports fan, Chicago is a great place to be year round, and especially in the fall if you’re into college sports. Chicagoans pull from many of the surrounding states and the city is a huge draw for many Big 10 university graduates. The city is such a magnet for Big 10 grads that many neighborhood bars throughout the city are specifically university-themed, such as a University of Michigan bar or an Ohio State or Wisconsin bar, showing that school’s big games and bringing out tons of alumni as a result.
Mamby on the Beach summer music festival
Things to Do
I touched on it briefly before, but if you’re in Chicago during any time of year, here are some highlights of the best activities the city has to offer:
Millennium Park
Go check out The Bean and several other of Chicago’s most famous sculptures, go ice skating during winter, and attend free outdoor concerts and movies in the park during summer.
Wrigley Field
Go see a Cubs game at Wrigley Field, or if you don’t have tickets, watch at one of the many sports bars in the area. Though Chicago’s other sports arenas aren’t located in Wrigleyville, stop by a Chicago Blackhawks, Bears, or Bulls game to get a taste of the city’s sports scene.
Wrigley Field
Museums
Chicago is known for being home to some of the best museums in the country. Be sure to check out The Field Museum, the Museum of Science and Industry, The Art Institute of Chicago, The Adler Planetarium, the Shedd Aquarium, and many more.
Magnificent Mile
The Magnificent Mile is the city’s primary commercial and shopping district, with upscale restaurants, hotels, and shops. Here you’ll find Chicago’s Water Tower Place shopping mall and can also access Chicago’s Riverwalk to enjoy an architectural boat tour, rent kayaks, or walk along the river, stopping at various bars and restaurants along the way. One of the area’s main attractions is the 360 Chicago Observation Deck at the John Hancock Center, which offers panoramic views of the entire city.
Hamilton at Chicago’s CIBC Theatre
Nightlife
No trip to Chicago would be complete without taking in the city’s wild nightlife! Experience some of Chicago’s many pubs, live-music, speakeasy, patio, and rooftop bars all over the city. For upscale nightclubs, the River North neighborhood will be your best bet.
North Avenue Beach
During the summer especially, North Avenue Beach is a can’t-miss destination. Sunbathe at the beach, play volleyball, go swimming in the lake, and walk or rent a Divvy bike and ride along the boardwalk.
Navy Pier
As a tourist, you’re required to stop by Chicago’s Navy Pier. Take a ride on the iconic ferris wheel and watch the fireworks Wednesday and Saturday nights during the summer.
Navy Pier
Other great things to do in the city are going to see a comedy show at the world-renowned Second City theatre, a Broadway show or a local theatre show, The Chicago Theatre for rotating stand-up comedians, concerts, and speakers, or the free Chicago zoo, which hosts ZooLights during the winter.
Tacos from Big Star in Wicker Park. Photo by @LaMordidaLatina
Classic Chicago Food and Restaurants
No matter what brings you to the city, you absolutely cannot leave without trying some of the foods and restaurants Chicago is famous for. Possibly the most famous and most important Chicago food to try is our Deep Dish pizza. Love it or hate it, Lou Malnati’s or Giordano’s are the two best places to give it a try.
You’ll also need to make sure to try a classic Chicago hot dog, preferably at The Wiener’s Circle, which is open late and has several locations throughout the city. Garrett Popcorn Shops gourmet popcorn is another must-try while in the city, and I would definitely recommend trying the traditional Garrett Mix, which combines their popular cheesecorn and caramel corn. Other notable restaurants to try are Chicago Pizza and Oven Grinder Company, Au Cheval for incredible burgers, BIG & Little’s for some of the city’s best tacos, and Sweet Mandy B’s if you have a sweet tooth.
Classic Chicago hot dog at Wrigley Field. Photo by Amy Pepe
If you’re looking for a beautiful American city with something for everyone, Chicago should definitely be high on your list. From food, to sports, to music, to nightlife, you’ll never be lacking for something exciting to do. Come check out Chicago and see what the Windy City is all about!
What an eclectic city! I had no idea. If you were a first time tourist with 2 days, what is your ultimate agenda? Including lodging.
Total budget for the weekend (including one night in a nice hotel, sightseeing, transport and food) is $800. Thanks in advance.
Hi Deirdre,
Thanks so much for reaching out!
With only two days in the city it’s so hard to choose! Based on your proposed budget, I would recommend staying at the Renaissance Chicago Downtown Hotel which is in the Loop right along the river. That’s about $230 per night and has live music at their rooftop bar and in the lobby (make sure to come when I’m playing!).
I would spend the first day heading north past the river and shopping along the Magnificent Mile and Water Tower Place (how you manage your budget here is up to you!) and then continue on to check out the zoo, which is totally free, grab lunch at Chicago Pizza and Oven Grinder, which shouldn’t put you out too much, and then walk off all that pizza along the lake (free). If you’re not exhausted by then, continue north to Wrigleyville for a Cubs game or explore the Lakeview neighborhood. Head over to the West Loop for dinner and try Piccolo Sogno, but be sure to make a reservation to sit out on the patio! Afterwards head over to Blind Barber speakeasy in the same area for a drink.
On day two, go for brunch at The Hampton Social in River North (a little pricey but totally worth it). Then explore The Field Museum or any of the other South Loop museums that interest you, admission ranges from $12-20 depending on which you choose. Take a walk around Millennium Park which is completely free, and then get ready for dinner at Cafe Babareeba in Lincoln Park for some incredible Spanish tapas. Next head west to the rooftop bar at Whiskey Business in Wicker Park for a drink. Take an Uber or the El back to your hotel to take in the beautiful Chicago Riverwalk at night. If you make it through even half of those things, I’d say you’ve done pretty well for yourself with only a weekend in Chicago!
Hope this helps 🙂
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