Chicago is one of those cities that feels like it has a little bit of everything. From incredible architecture and deep-dish pizza to baseball games, museums, comedy, and amazing restaurants, there is no shortage of things to do.

In April, I spent a few days in Chicago for my birthday and 2 year anniversary and packed my trip with a mix of sightseeing, food, culture and a Cubs game at Wrigley Field in just a few short days. If you’re planning a Chicago weekend getaway, here are some of my favorite things we did, where we ate, and a few additional Chicago recommendations to add to your list.

A little disclaimer before we get started: This was my first time visiting Chicago, so this guide is based on what I was able to experience during my trip, along with a few recommendations from friends. I'm sure there are so many other amazing restaurants, bars, neighborhoods and things to do that I didn't get a chance to see. I already know I'll need to come back to Chicago to explore more of the city and of course, eat at all of the places I missed!

WHERE TO STAY IN CHICAGO

There are so many great hotels in Chicago, and where you stay can really change the feel of your trip. For a first visit, I would look for somewhere around Michigan Avenue, the Chicago River, or the Riverwalk so you can easily walk to many of the main attractions. These are seven hotels I had on my list, from a more affordable option to a full luxury stay.

CITIZENM CHICAGO DOWNTOWN

Address: 80 E. Wacker Pl, Chicago, IL 60601

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Where we stayed! The location was fantastic — you're just a short walk from the Riverwalk, Millennium Park, The Bean, the Art Institute, and Michigan Avenue. The rooms are definitely on the smaller side, but they're modern, clean, and have everything you need if you're planning to spend most of your time out exploring the city. It's a great option if you want a convenient downtown location without spending a fortune.

LONDONHOUSE CHICAGO

Address:‍ ‍85 E. Wacker Dr, Chicago, IL 60601

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This was actually the hotel I wanted to stay at! LondonHouse is right on the Chicago River at Michigan Avenue and is known for its incredible rooftop, LH Rooftop. The location is perfect for a first trip, with the Riverwalk, Millennium Park, Magnificent Mile, and Art Institute all within walking distance. The rooftop views alone would make me want to stay here next time.

CHICAGO ATHLETIC ASSOCIATION

Address:‍ ‍12 S. Michigan Ave, Chicago, IL 60603

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If you want a hotel with a little more character, this is a great choice. The historic building is directly across from Millennium Park and the Art Institute, so the location is hard to beat. The hotel also has several restaurants and bars, including Cindy's Rooftop, making it feel like part of the Chicago experience rather than just somewhere to sleep.

RIVER HOTEL CHICAGO

Address:‍ ‍75 E. Wacker Dr, Chicago, IL 60601

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If location is your biggest priority, this is one to consider. River Hotel is right along the Chicago River and just steps from the Riverwalk, Michigan Avenue, and many of the city's main attractions. It's a more approachable option than some of the luxury hotels, so it's worth checking out if you want to be right in the middle of everything without spending as much.

THE LANGHAM CHICAGO

Address:‍ ‍330 N. Wabash Ave, Chicago, IL 60611

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If you're looking to splurge, The Langham would be at the top of my list. It's a beautiful luxury hotel right along the Chicago River with spacious rooms, river and skyline views, a spa, indoor pool, and afternoon tea. It's definitely a step up in price, but if you're celebrating something or want the hotel itself to be part of the experience, this would be such a special choice.

KIMPTON GRAY HOTEL

Address: 122 W. Monroe St, Chicago, IL 60603

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If you want something boutique, stylish, and a little more luxurious, the Kimpton Gray is a great option. It's located in the Loop in a historic building, but the inside has a much more modern feel. I also love that it has Boleo, a rooftop bar and lounge, along with Vol. 39 for cocktails, so you don't have to go far for a drink after a day of sightseeing.

PALMER HOUSE, A HILTON HOTEL

Address: 17 E. Monroe St, Chicago, IL 60603

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If you want to stay somewhere with a lot of Chicago history, the Palmer House is such a fun option. This iconic hotel has been in Chicago for more than 150 years and is right in the heart of the Loop, just two blocks from the Art Institute and Millennium Park. The grand lobby is gorgeous, and the hotel is also famous for being the birthplace of the Palmer House brownie!

THINGS TO DO in Chicago

Architecture Tour

One of my favorite things we did in Chicago was an architecture boat tour with the Chicago Architecture Center.

Chicago is famous for its architecture, and seeing the skyline from the river gives you a completely different perspective. The tour was such a fun way to learn more about the history and design behind some of Chicago’s most recognizable buildings without feeling like a traditional history lecture. Even if architecture isn’t something you would normally seek out while traveling, I would still recommend putting this on your Chicago itinerary. The buildings along the river are incredible, and you’ll get some of the best views of the Chicago skyline from the water.

CATCH A GAME AT WRIGLEY FIELD

Address: 1060 W. Addison St, Chicago, IL 60613

No trip to Chicago would feel complete without experiencing a Cubs game at Wrigley Field. Wrigley Field is one of those places that feels like an experience even if you’re not the biggest baseball fan. The historic ballpark is surrounded by classic Chicago buildings, neighborhood bars, and restaurants making it easy to turn game day into an entire afternoon or evening. As a girlfriend of a mega Mets fan it was quite disappointing to see the Cubs sweep the Mets but I did love the cute song the fans sing after a win.

SPEND AN AFTERNOON AT THE CHICAGO ART INSTITUTE

Address: 111 S Michigan Ave, Chicago, IL 60603

Tickets for the Guided Tour at the Museum Here!

Chicago has so many incredible museums that you could easily spend an entire day exploring one. We spent part of our trip visiting the Chicago Art Institute pretending to be Ferris Bueller. I always like having at least one museum or cultural stop when I travel because it gives you a chance to slow down.

One of the best parts about visiting is getting to see so many iconic works that you've probably seen before without realizing they were housed in Chicago. Some of the museum's most famous pieces include Grant Wood's American Gothic, Edward Hopper's Nighthawks, Georges Seurat's A Sunday on La Grande Jatte—1884, Vincent van Gogh's The Bedroom, Claude Monet's Water Lilies, and Katsushika Hokusai's The Great Wave. The museum also has Georgia O'Keeffe's enormous Sky above Clouds IV, which stretches about 24 feet across and is one of the museum's most recognizable works.

SEE A SHOW AT THE SECOND CITY

Address: 1616 N. Wells St., Chicago, IL 60614

If you’re looking for something fun to do at night, add a show at Second City to your Chicago itinerary.

The Second City is famous for its improv and sketch comedy and has been a major part of Chicago’s comedy scene for decades. We went to a show during our trip and was one of the highlights of the entire trip. Anytime I go to Chicago I’m adding this to my itinerary. It’s like if every SNL skit was funny.

WHICH SECOND CITY SHOW SHOULD YOU SEE?

If you’re overwhelmed by all of the different show options, a recommendation I received was to look for The Mainstage 114 Revue. It’s The Second City’s feature show and a great choice if you’re looking for the classic Second City experience.

For tickets, General Admission is a great option. While it’s not the cheapest ticket category, you’re more likely to get a good view of the stage. Some of the less expensive Value seats can have obstructed views, while Premium seating is closer to the front.

MILLENNIUM PARK & THE BEAN

You can't visit Chicago for the first time without stopping by Millennium Park and seeing Cloud Gate, better known as The Bean. It's one of those places that is definitely touristy, but for good reason! The Bean is one of the most recognizable landmarks in Chicago and is a fun spot to grab some photos while you're exploring downtown. Millennium Park is also right next to the Art Institute of Chicago, so I would definitely combine the two in the same part of your day. After visiting the museum, you can walk through the park, see The Bean, and continue exploring the area around Michigan Avenue.

WALK THE CHICAGO RIVERWALK

Address: Lake Michigan and Lake Shore Drive to Lake Street

The Chicago Riverwalk is another easy addition to your Chicago itinerary, especially if you're already planning to do the architecture boat tour. The Riverwalk runs along the Chicago River through downtown and gives you some really great views of the city's architecture from a completely different perspective. There are restaurants, bars, seating areas and plenty of spots to stop and take in the views along the way. I would recommend walking the Riverwalk around sunset if you can — the buildings reflecting off the river make for such a pretty view. You can also easily combine this with an architecture cruise, since you'll already be spending time along the river.

EXPLORE THE WEST LOOP

If you're looking for a neighborhood with great restaurants, cocktails, and a fun atmosphere, definitely add the West Loop to your Chicago itinerary. This was one of my favorite areas for going out because you can easily spend an entire evening here without having to travel all over the city. Fulton Market is filled with restaurants, bars, and places to grab a drink, and there are so many different options depending on what you're in the mood for. We went to Aba and Trivoli Tavern while we were in the area and there are plenty of cocktail spots nearby too, including Lazy Bird and Bisous. I would definitely recommend planning a dinner and drinks night in the West Loop — especially if you're looking for a fun area that feels a little more local than the typical downtown tourist spots.

WHERE TO EAT IN CHICAGO

There are so many good restaurants in Chicago that I quickly realized I was never going to be able to try them all in one trip. Between the incredible Italian food, deep-dish pizza, steakhouses, sushi, Mediterranean restaurants, and cozy cocktail bars, there are way too many places I want to try. I already know I'll need to come back to Chicago just to eat my way through more of the city! Here are the restaurants we tried during our trip, along with a few recommendations that were too good not to add to the list.

GILT BAR

Address: 230 W. Kinzie St, Chicago, IL 60654

I celebrated my 31st birthday at Gilt Bar and it was one of my favorite restaurant stops in Chicago. The atmosphere is dark, moody, and sophisticated, making it a great option for dinner or drinks. It’s the kind of restaurant where the ambiance is just as memorable as the food. Gilt Bar has been recognized by the Michelin Guide with a Bib Gourmand, which is awarded to restaurants offering good quality food at a good value.

Don’t forget to use the photo booth downstairs!

TRIVOLI TAVERN

Address: 114 N. Green St, Chicago, IL 60607

It’s cozy, lively, and has that old-school Chicago atmosphere that makes you want to stay for another drink. It’s a great place to add to an evening of exploring the city, especially if you’re looking for somewhere that feels fun without being overly formal.

The Sticky Date Cake is the dessert I would absolutely recommend saving room for. It's served with date crumble, brown butter ice cream, and toffee sauce and it is SO good. Trivoli Tavern is also owned by the same group of Gilt Bar - they have some overlapping menu items.

ELINA’S

Address: 1202 W. Grand Ave, Chicago, IL 60642

Elina’s was another dinner stop during our Chicago trip. The restaurant has a warm, intimate atmosphere and makes for a great dinner option if you’re looking to experience some of Chicago’s neighborhood dining scene. Fun fact! The owner of Elina’s worked closely with the group who opened Carbone.

ABA

Address: 302 N. Green St, 3rd Floor, Chicago, IL 60607

Located in Chicago’s West Loop, the restaurant has a beautiful, lush feel that almost makes you forget you're in the middle of the city. The rooftop patio is especially gorgeous.

The menu is Mediterranean-inspired and meant to be shared, so it's the perfect place to order a bunch of different things for the table. The crispy short rib hummus and whipped feta is a 10/10.

TOPO GIGIO

Address: 1516 N. Wells St, Chicago, IL 60610

Topo Gigio is a great option for dinner before a show. It’s located in Old Town and is just a short walk from The Second City, making it an easy pairing for a night out.

PORTILLO’S

Address: 100 W. Ontario St, Chicago, IL 60654

Portillo’s is famous for Chicago-style hot dogs, Italian beef sandwiches, and other classic Chicago comfort food. Even if you already have a packed restaurant itinerary, I’d make time for a quick stop here.

BAVETTE’S BAR & BOEUF

Address: 218 W. Kinzie St, Chicago, IL 60654

If you’re looking for a steakhouse in Chicago, Bavette’s is one I’d put high on the list. Reservations can be difficult to get, so one recommendation is to try walking in right when they open at 4 PM. It can be a good strategy if you weren’t able to snag a reservation.

SUSHI-SAN

Address: 63 W. Grand Ave, Chicago, IL 60654

For sushi, Sushi-San downtown is another recommendation to save. It’s a great option if you’re craving something different from the classic Chicago staples.

QXY DUMPLINGS

Address: 2002 S. Wentworth Ave, Suite 103, Chicago, IL 60616

If you love dumplings, add QXY Dumplings to your list. They are especially known for their soup dumplings, and it’s a great place to stop while exploring Chinatown.

THE GREAT CHICAGO DEEP-DISH PIZZA DEBATE

When most people think of Chicago, they immediately think of deep-dish pizza. It's probably the city's most famous food and trying a slice is almost considered a rite of passage for first-time visitors. But here's something that might surprise you: deep dish isn't necessarily what most Chicagoans are eating on a regular basis. Chicago's everyday pizza tradition is actually tavern-style pizza — a much thinner, crispier crust that's traditionally cut into small squares. Deep dish is more of an occasional meal and there is a pretty big debate among locals about which style of pizza is actually the best.

And then there's a second debate: which restaurant makes the best deep dish? Ask a Chicagoan and you're likely to get a very strong opinion.

SO, WHERE SHOULD YOU GET DEEP DISH?

There isn't one universal answer, which is what makes the Chicago pizza debate so fun. Some of the biggest names you'll hear are Lou Malnati's, Giordano's, Gino's East, Pizzeria Uno, Pizzeria Due, and Pequod's. But these aren't all exactly the same style of pizza, which is where things get confusing.

Lou Malnati's signature Buttercrust is flaky and buttery, and their Chicago Classic comes with sausage and extra mozzarella. It's the traditional version most people picture when they hear "Chicago deep dish."

Giordano's is another famous Chicago name, but technically they are known for stuffed pizza. Their pizza has an additional thin layer of dough underneath the sauce, creating an especially cheesy, substantial pie. If you're looking for the dramatic cheese-pull pizza you see all over Instagram, this is probably the one you're imagining.

We went to Pequod's during our trip and I quickly learned that even calling it "deep dish" can start an argument. Pequod's makes a pan-style pizza with its famous caramelized cheese crust. Cheese is pushed all the way to the edge of the pan, where it becomes browned, crispy, and almost caramelized against the crust. It was great and I was not disappointed!

If you're visiting Chicago, you should absolutely try deep dish at least once. Even if it's not what locals are eating every week, it's part of what makes Chicago famous.

COCKTAIL BARS IN CHICAGO

CINDY’S

Address: 12 S. Michigan Ave, Chicago, IL 60603

Cindy’s is a rooftop bar with incredible views overlooking Millennium Park and the Bean. It’s a great spot to grab a cocktail and take in one of the best views in downtown Chicago.

THREE DOTS AND A DASH

Address: 435 N. Clark St, Chicago, IL 60654

If you’re looking for something completely different, check out Three Dots and a Dash. This tiki bar in River North is known for creative cocktails and a fun, tropical atmosphere. It’s a great place for a more unique Chicago night out.

BEATNIK ON THE RIVER

Address: 80 N. Upper Wacker Dr, Chicago, IL 60606

Beatnik on the River is right along the Chicago River and is another beautiful spot for cocktails. It could also be a great option for brunch if you’re looking for somewhere to start your day. The lush, eclectic atmosphere makes it feel completely different from your typical downtown restaurant.

GUS’ SIP & DIP

Address: 51 W. Hubbard St, Chicago, IL 60654

Gus’ Sip & Dip may sound a little kitschy, but don’t let the name fool you. It’s a great cocktail bar in River North with genuinely good drinks and some of the more approachable cocktail prices downtown. It’s also a nice option when you don’t have a reservation and want to spontaneously stop somewhere for a drink.

LAZY BIRD

Address: 200 N. Green St, Chicago, IL 60607

Located in the cellar level of The Hoxton Chicago, Lazy Bird is a cocktail and music lounge in the heart of Fulton Market. The combination of cocktails and live jazz makes this a great option for a night out, especially if you’re looking for something a little more intimate.

BISOUS

Address: 938 W. Fulton Market, Chicago, IL 60607

Bisous is a French-inspired cocktail bar in Fulton Market with a romantic Parisian feel. The space is beautiful, and the cocktail menu focuses on classic-inspired drinks. It’s a great stop for a pre-dinner cocktail or a nightcap.

LH ROOFTOP AT LONDONHOUSE

Address:85 E. Wacker Dr, 22nd Floor, Chicago, IL 60601

If you're looking for a rooftop with an amazing view, LH Rooftop at LondonHouse is definitely worth adding to your Chicago list. Sitting right along the Chicago River, the rooftop has beautiful views of the river, the Wrigley Building, Michigan Avenue, and the Chicago skyline. It's especially pretty around sunset when the city starts to light up.

Final Tips

Chicago completely lived up to the hype for me. What I loved most was how different each part of the trip felt. One minute we were learning about the city’s incredible architecture, the next we were sitting at Wrigley Field watching a baseball game, and then ending the day with an amazing dinner or comedy show.

If you’re planning a Chicago trip, I wouldn’t try to see absolutely everything. Instead, pick a few of the city’s iconic experiences and leave yourself time to wander, eat, and enjoy the city along the way.

And don’t be afraid to venture outside of downtown. From Old Town and Chinatown to the West Loop and Wrigleyville, some of the best restaurants, bars, and experiences are spread throughout Chicago’s different neighborhoods.

From the architecture to Wrigley Field to the food, Chicago is a city that makes it very easy to break from the routine.

Planning your next trip? Check out my other travel guides for more itineraries, restaurants, and things to do on your next adventure.

XOXO

Jenna