4 Days in Chicago: Ultimate Travel Guide

So, you're going to Chicago or want to plan a trip. What to EAT in Chicago? What to SEE in Chicago? What to DO in Chicago? Keep reading to find the answers to all your questions and make the most out of your vacation in this 4 Days in Chicago: Ultimate Travel Guide.

Chicago has been on my travel bucket list for a while, so when I had the opportunity to travel there for a food blogger conference, I knew I had to go. Since I was traveling for work, I made sure to add in enough time to explore and experience the city.

Other than the two days I attended the conference, my husband and I had two and a half days to be tourists, so we had 4 days in Chicago! We packed our days full of food and fun, and we were able to see a lot!

Where to STAY in Chicago?

We stayed at the Chicago Athletic Association Hotel. This Venetian Gothic style building is a boutique hotel with 241 rooms. The architecture and ornate interior are breathtakingly beautiful. From the hotel rooftop restaurant and bar, Cindy's, you can take in the views of the Chicago skyline and Lake Michigan. This hotel is conveniently located across the street from Millennial Park and within walking distance to an "L" train station and numerous Chicago attractions and restaurants.

I found the history of the Chicago Athletic Association building to be interesting as well. It originally opened in 1893 as a private athletic club for Chicago’s most rich and powerful men. The building was repurposed as a boutique hotel in 2015 and now their doors are open to everyone.

We were thrilled with our hotel choice. The service, views, and location were exactly what we hoped for. In my opinion, the only downside to this hotel was wait time due to slow elevators and a smaller than average room size.

Where to EAT in Chicago?

I came to Chicago to eat! All of our meals were delicious and we were not disappointed with any of the food. I researched Chicago's best restaurants and made reservations at a couple. If you have a specific restaurant and date/time in mind, you should make reservations about a month in advance. I made reservations two weeks in advance and still had a difficult time getting in everywhere we wanted. Where we ate in Chicago:

The Purple Pig

Since opening in 2009, The Purple Pig has been recognized on numerous "Best Restaurant" lists around the city and the country. The chef, Jimmy Bannos Jr., was dubbed the "Prince of Pork" and named James Beard, Rising Star Chef of 2014. The Purple Pig has been on my "bucket list" of Chicago restaurants for a while. The menu showcases the Mediterranean flavors of Italy, Greece, and Spain. The service and the food were both amazing and we left with full hearts and bellies.

Favorite plates: Grilled Broccoli with Anchovy Vinaigrette and Milk Braised Berkshire Shoulder
Would we return to this restaurant? YES

Girl & the Goat

Girl and the Goat was the first reservation I made when planning our trip to Chicago. I'm a huge fan of the Bravo show Top Chef, so I knew I wanted to visit the restaurant of season 4 winner, Stephanie Izard. Although the service felt very rushed (we were in and out in under an hour), the small plates they serve were innovative, delicious, and made for sharing. My husband and I ordered four plates to share.

Favorite plates: Goat Empanadas and Roasted Oysters with Sausage Butter
Would we return to this restaurant? Most likely - I'm curious to return to try other dishes and hope that service won't be uncomfortably rushed next time.

The Gage

The Gage was a pleasant surprise because we didn't have reservations or plan to eat there. We simply chose the restaurant for dinner one night because it was conveniently located next door to our hotel, the Chicago Athletic Association. The Gage's inventive American menu ended up being one of my favorite meals. The atmosphere was lively and romantic with candles lit at each table. We tried a lot of food here! We ordered two appetizers, two entrées, and a huge dessert to take back to our hotel room.

Favorite plates: Mussels appetizer, Salmon entrée, and Apple Cobbler with Bourbon Ice Cream
Would we return to this restaurant? YES

Testaccio

Testaccio is Southern Italian comfort food at it's finest! My cousin lives in Chicago and she suggested we eat at this restaurant, so you know it's "local approved". Testaccio opened in the summer of 2020, and the owner has a second restaurant right up the street in Logan Square named Osteria Langhe. Since my cousin was dining with us and we wanted to try everything we could, we ordered 5 plates to share. I'm still dreaming about the table of delicious food we received.

Favorite plates: Smoked Lamb Meatballs, Roman Artichokes, and Mezze Maniche al Sugo di Manzo (red wine braised ox tail and beef ragu)
Would we return to this restaurant? YES

Cindy's Rooftop

Cindy's Rooftop is the stylish restaurant and bar located at the top of the Chicago Athletic Association Hotel. Technically, we didn't eat a full meal here, but we did order drinks and chocolate chip cookies! Since we were staying at the hotel we went to get drinks here twice - both times were very crowded and took a little waiting at the bar. The view is worth it! Cindy's Rooftop has one of my favorite views of Chicago - from the heated outdoor patio on the 13th floor you can see Cloud Gate (aka "The Bean") in Millennial Park, skyscrapers, and Lake Michigan. The chocolate chip cookies were delicious as well!

Favorite plates: the cookies 🙂
Would we return to this restaurant? YES- The dinner menu didn't appeal to me, but it changes seasonally, so it may sound tastier next time. Whether we eat there or not, I would definitely go back for the cookies and the view!

Goddess and the Baker

The Goddess and the Baker has multiple locations all over town. We frequented the one located right around the corner from the Chicago Athletic Association Hotel and Millennial Park. Move over Starbucks (we literally walked passed a Starbucks to get coffee here!) Not only was it a convenient walk, but the coffee is a absolutely delicious any way you order it. JJ doesn't like coffee so he ordered their version of hot chocolate - it's called liquid chocolate. Their liquid chocolate is a thick, velvety drink and it almost tastes like you are drinking a melted candy bar. We went here a couple times during our stay and even ordered a quick, satisfying breakfast here one morning.

Favorite: Mayan Mocha (warning: it's spicy)
Would we return to this restaurant? YES- and we did multiple times during this vacation

Rosebud Randolph

Rosebud on Randolph was another restaurant that wasn't planned but pleasantly surprised us. The restaurant we were planning to go to for brunch was packed with a line out the door on a cold, windy Sunday morning. Thankfully, we noticed Rosebud serving brunch right next door with no wait time. Of course, JJ found ice cream on the menu and ordered the Bananas Foster French Toast with Vanilla Gelato. JJ let me try a bite and it was so good I had to keep going back for more! My crab cakes were ideal - moist, flavorful, and full of crab meat!

Favorite plates: Bananas Foster French Toast and Crab Cake Benedict
Would we return to this restaurant? YES

Lou Malnati's

Of course, a classic Chicago-style deep dish pizza was on my " food bucket list" and I heard Lou Malnati's was the best. It was... fine. It was a fun experience and I'm happy to check it off my bucket list. If you go, give yourself enough time as the pizza takes about 40 minutes to make. We ordered two personal sized deep dish pizzas - one with sausage (the "Malnati Chicago Classic") and one with pepperoni. We both thought the sausage pizza was better. The sauce was flavorful, but the cheese was a little too chewy for my liking and the crust wasn't as buttery soft as I was hoping for.

Favorite plate: Sausage deep dish pizza
Would we return to this restaurant? No - but it was a good one-time experience

Portillo's

A Chicago-style hot dog was another item on my "food bucket list". A classic Chicago-style hot dog includes mustard, relish, celery salt, onions, sliced tomatoes, kosher pickle and sport peppers piled onto a poppy seed bun. I read that Portillo's had the best, and it did not disappoint! Their menu is huge and offers a variety of sandwiches, burgers, and pasta, in case you're not in the mood for a hot dog.

Favorite plate: Chicago-style hot dog
Would we return to this restaurant? YES - the hot dog was delicious and I'm curious to try more food items on their menu

What to DO in Chicago?

Chicago has so many fun and unique activities to keep you entertained. Although we were only there for a few short days, we packed in as much as we could. To be honest, I was exhausted at the end of this trip, but happy that I was able to see (almost) everything on my Chicago bucket list. Keep in mind, there are hundreds of things to do, but this is what we did in Chicago:

Chicago River Architecture Boat Tour

The Wendella Architecture Boat Tour along the Chicago River was one of our favorite activities in Chicago. We boarded a large open air boat and sailed comfortably down the river listening to a humorous, knowledgeable tour guide. The narrated tour focused on Chicago's architecture and history. We sailed on the 90-minute boat tour, but they also offer shorter 45-minute tours as well. The boat was great, no seat had a bad or obstructed view.

Cost: $40 per adult on the 90-minute tour

The Second City - Comedy Club

Get ready to laugh! The Second City opened it's doors in 1959 and has grown to be a comedy empire. Many well-known comedians got their start and performed at Second City, such as: John Belushi, John Candy, Bill Murray, Dan Aykroyd, Chris Farley, Amy Sedaris, Stephen Colbert, Bonnie Hunt, Steve Carell, Tina Fay, and seriously, the list goes on and on. They offer a wide variety of hilarious stand-up, sketch, and improv shows. We saw two comedy shows at Second City - "Clued In" and "Together at Last." Both shows were fun, engaging, and had us laughing out loud.

Cost: around $25 - $60 depending on the date and show you chose

The Art Institute of Chicago

Founded in 1879, the Art Institute of Chicago is one of the largest and oldest museums in the world. It houses the largest collection of Impressionist and Post-Impressionist art outside of the Louvre. It's home to more than 300,000 pieces of art, including some of the world's most well-known masterpieces. The walls are filled with artists, such as Picasso, Van Gogh, Monet, O'Keefe, Pollock, and Warhol. It's amazing to be standing so close to a piece of art history. You could spend an entire day walking through this museum. Give yourself enough time to explore everything - we visited on a Sunday morning and spent about 3 hours in the museum.

Cost: $25 for out of state adults

Observation Decks: Skydeck Chicago vs. 360 Chicago

Both observation decks offer breathtaking, expansive views of the city and an educational experience before the main event. Skydeck and 360 Chicago are similarly priced and offer similar views. Personally, I preferred the interactive educational experience and The Ledge experience at Skydeck making that my favorite observation deck of the two.

Skydeck Chicago at Willis Tower

The Skydeck is located on the 103rd floor of Willis Tower, the eighth tallest building in the world. Before getting on the elevator to the Skydeck, visitors walk through an interactive and educational attraction that highlights the iconic building and celebrates Chicago sports, architecture, pop culture, history, food, music and people. Although we went to the Skydeck during the middle of a workday on a Wednesday, the elevator to the top was packed full of people. From the Skydeck you can look down to see beautiful, extensive views of the city and surrounding buildings.

My favorite part of the Skydeck experience was walking out on The Ledge. The Ledge is a fully enclosed window that juts out a few feet and allows you to walk over the city for a daring and unique view from 103 floors in the air. Luckily, The Ledge was not too busy when we visited which allowed us to spend more time standing above the city. Keep in mind that during busy hours you are limited to 60 seconds on The Ledge.

Cost: $30 per person (prices can vary by day and age)

360 Chicago at John Hancock Building

360 Chicago allows you to view the city and Lake Michigan from the 94th floor of the John Hancock building. Similar to the Skydeck experience, 360 Chicago walks you through an educational tour of the city before you take the elevator to the main attraction at the top. Personally, I preferred the more interactive attraction before the Skydeck experience. The view from 360 Chicago differs slightly from the Skydeck because at 360 Chicago you are at the edge of Lake Michigan, while Skydeck is in the heart of the city. We enjoyed being so close to the water and looking out at one of the Great Lakes.

360 Chicago offers the TILT experience which is known as "Chicago's highest thrill ride." TILT extends over the side of the building giving visitors a unique downward view of the city below. Unlike the Skydeck, the 94th floor of the John Hancock building has a bar and numerous tables and chairs. After walking all over the city, I enjoyed being able to sit for a while with a drink in my hand at Bar 94.

Cost: $30 (more if you add a drink ticket or TILT experience)

FREE Attractions in Chicago

Cloud Gate (aka "The Bean") in Millennial Park

Millennial Park offers many attractions (ice skating, rock wall, putt putt golf, etc.) and Cloud Gate is one of the most popular. Cloud Gate was unveiled in 2004 and is one of the largest permanent outdoor art installations. The shiny, stainless steel exterior reflects city skyscrapers on one side and the green space of the park on the other. The Bean is 33 feet high, 42 feet wide, and 66 feet long. It weighs about 110 tons.

Chicago Riverwalk

Get your walking shoes on! The Chicago Riverwalk is a 1.25 mile long multi-use public space. Public art, water activities, playscapes, and restaurants can be found along the Riverwalk. Each section of the Riverwalk has its own theme.

Magnificent Mile

Keep your walking shoes on and head to the Magnificent Mile. The Magnificent Mile is a 0.8 mile strip of Michigan Avenue and is Chicago’s premier commercial district. The vibrant, bustling area is home to upscale shops, trendy restaurants and posh hotels.

Save Money with CityPASS

If you plan to visit multiple top Chicago attractions, consider buying a CityPASS ticket. You can pay to get entry into either 3 or 5 top attractions and save money by buying in bulk.

Transportation

Chicago is a very walkable city, so make sure to pack comfortable shoes to walk around town. If your destination requires a longer commute, try to ride the "L" train everywhere you can. The "L" stands for elevated because most of the trains run elevated above the city streets.

Taxis and Uber are very easy to find as well, but they will be much more expensive than a train ride. Originally, I had planned to Uber around town until I realized how convenient and cheap the "L" was to ride. We bought the $5 day pass daily which allowed us unlimited use of the train and bus system. You can get to almost any destination I mentioned above by riding the train or a bus. At the end of our vacation, we even rode the train to the airport.

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