Chicago for Foodies
Chicago, Illinois Travel Itinerary & Guide
Itinerary Created By:
4 Days in Chicago, Illinois, USA
Discover the best food, nightlife and more with this wonderful guide and day-by-day itinerary for Chicago, Illinois. We spent Labor Day Weekend in Chicago exploring the Windy City.
Day 1:
We arrived in the evening in Chicago and after checking into our hotel were eager to start exploring!
Hyatt Place Chicago Downtown The Loop
We checked into the Hyatt Place Chicago Downtown-the Loop which is a stylish, yet affordable hotel in a perfect location. We were initially on the 3rd floor, but they were able to get us a room all the way at the top. Would absolutely recommend this hotel! Breakfast is included and there is a gym/pool as well.
Lou Malnati's Pizzeria
Start your adventure off right with the famous Chicago Deep Dish Pizza from Lou Malnati’s. (By the way, we love pizza so you’ll be getting a lot of it with this itinerary!) We thought it would be a long wait to get a table, but it was less than a 15-minute wait time. You can also order your pizza while you wait for your table, which makes things a lot quicker as it can take over 30-45 minutes to make a pizza. We ended up ordering our pizzas after we sat down (rookie mistake) but to make the time pass we got to enjoy a refreshing Malnati salad (Romaine lettuce, tomatoes, black olives, mushrooms, salami bits, and gorgonzola cheese with Sweet Vinaigrette and romano cheese). Then for the grand finale, we had the Malnati Chicago Classic (sausage, some extra cheese and vine-ripened tomato sauce on butter crust) and the Lou (Spinach mix, mushrooms and sliced Roma tomatoes covered with a blend of mozzarella, romano, and cheddar cheese on garlic butter crust). They were delicious, but we made another rookie move and ordered two personal pizzas to share thinking that a larger size would be too much food. We should have done two smalls and left overstuffed (you’ll do a lot of walking in Chicago so it will make you feel a little better after eating all this).
Photo courtesy of Lou Malnati’s.
The Library
The Library is a hidden gem located under the Gilt restaurant. See a hostess at the Gilt who will hopefully have space for you downstairs in the hidden speakeasy. The hostess will guide you downstairs towards the restroom in a hallway filled with photobooth pictures and will then surprise you with a secret door that leads to an intimate cocktail lounge and restaurant. With jazz music filling your soul and wonderfully perfected craft cocktails all while feeling in a dream-like state with the candlelight, you’ll quickly realize this place is a hidden gem.
The Old Crow
Old Crow Smokehouse is a restaurant turned bar at nighttime with live music and great drink specials. It happened to be packed on a Thursday night as the local MBA programs will sometimes host mixers there.
Three Dots and a Dash
We have tiki bars in San Francisco but nothing like Three Dots in a Dash. Most tiki bars are cheesy and well straight up trashy, but Three Dots in a Dash is a tiki bar done right! The entrance is hidden down an alleyway that can be hard to find, but once you find the alleyway you’ll immediately spot the entrance illuminated with tiki torches. From the moment you enter you are transported to another world. Make your way downstairs descending past the plethora of skulls and to the bar area, where you’ll be greeted with great music and an even better craft cocktail list, of course, all the drinks being tiki themed. Luckily, it’s not all rum (I do love my rum, but some nights you have to switch it up!) If you have a larger group, there are really well-crafted cocktails to share! The bartenders put a great effort into making their cocktails and it shows by their presentation and great taste. I would recommend a drink here and maybe to even hit up their dance floor.
Day 2:
Enjoy exploring some of the most notable parts of Chicago. Be sure to wear comfortable walking shoes and dress for outdoor weather.
Wildberry Pancakes & Cafe
Grab a delicious brunch at Wildberry Cafe next to Millennium Park. I don’t believe they take reservations, but if you have the Yelp app, you can add your name to the wait list. We added our name to the wait list and were quoted a one-hour and a half wait time which really turned into two hours. (Pro-tip: Add your name to the waitlist as soon as you wake up!) Even though there is a long two-hour wait, we had plenty of time to explore Millennium Park. Now let’s focus on the food, Wildberry Cafe’s food is delicious, and the best part is that most entrees come with a side of pancakes! Yes, you can have your cake and eat it too! We ordered the Butcher Block skillet (hash browns, cheddar & jack cheese, two eggs, ham, sausage, turkey sausage, chicken sausage, and bacon)…meat eaters rejoice! We subbed specialty pancakes because go big or go home and almost cried over how good the banana coconut cream pancakes were. We also ordered the Wild Mushroom omelet (provolone cheese, prosciutto ham, herb roasted cremini, oyster and shitake mushrooms) and a specialty order of the chocolate chip banana pancakes. Everything we had was perfect, and I hope to get the chance to enjoy it again soon! Just note, it’s a lot of food and will probably carry you over through lunch (think of it as a two-for-one special).
Milenium Park
Take a stroll through the world-famous Millennium Park. (You could even do this while waiting for a table at Wildberry.) Some notable sites to visit are Cloudgate (a.k.a. the bean as the locals call it, be sure to flick it), Jay Pritzker Pavilion (a beautifully futuristic amphitheater), Buckingham Fountain (one of the most stunning and grand fountains in the world-there are night light shows as well), Crown Fountain (a popular fountain for children to play in on a hot day, two faces are shown on giant screens and if you wait long enough they’ll even shoot water out of their mouths). There are also many other parks, trails, and even a roller rink to get lost in. We actually ended up at Millennium Park multiple times! There are also sometimes great events taking place. When we visited there was Jazz Fest which was free for the public to enjoy.
Day 3:
Getting closer to Taupo : Huka falls, sunny brunch close to the lake and afternoon dip into natural hot springs.
Lakeside Walk
There are many paths and trails from Millennium Park to the lakeside walk. It’s enjoyable to look out at the water and see all the different boats along the shore. You can rent kayaks or paddle boards, and even some boats are bars that you can stop in on for a drink. There are dedicated walking paths and biking paths if you wanted to rent a bike as well.
The Riverwalk
The Riverwalk is a new installation and will absolutely be a center of socializing for Chicago, especially on the rare warm summer days. The riverwalk was built very recently, and each section has a different theme as well as cocktails bars. The cocktail bars are a bit expensive, but you can’t pass up a cocktail with these incredible views and atmosphere. Since we went Labor Day weekend and it was hot out, every single bar was packed, which actually made it more fun to people watch and enjoy a nice cocktail or beer. We grabbed a drink at the first bar Tiny Tapp, but wanted to explore some more but didn’t have the time. I would dedicate some time in the afternoon when everyone is getting off of work to enjoy this great area!
Architecture River Cruise: Chicago's First Lady Cruises
Close to the riverwalk you can join an Architecture River Cruise, which was recommended to us by everyone who has visited Chicago and even by locals. A lot of people recommend going for the sunset cruise at it offers some picturesque views of the city with beautiful lighting. We elected to use First Lady Cruises, as suggested by friends, they offered a lot of departure times and left from the Riverwalk as opposed to Navy Pier (which we were told is the worst tourist trap you can visit in Chicago). The architecture river cruise is fascinating and very enjoyable as Chicago has some of the most beautiful and historic architecture in North America…there is also a bar onboard because any cruise is a booze cruise if you try hard enough! You can buy your tickets online for a discount and avoid the ticket counter lines.
The Purple Pig
The Purple Pig was our favorite meal in Chicago. Every dish was so delicious and served perfectly. The menu is quite diverse, but it’s centered around small share plates (my favorite) that come out as they are prepared. We ordered the corn risotto, Octopus A La Plancha, Chicken Thigh Kebabs, Milk Braised Berkshire Shoulder, and the Bavette Steak. Our favorite item on the menu was the Milk Braised Berkshire Shoulder as it just melted in your mouth with each bite, but I would absolutely recommend everything we had from the crispy skin on the chicken thigh kebabs to the perfectly cooked Bavette steak. If you’re in Chicago, you have to go here for dinner. Just to note they don’t take reservations but you can put your name down and they’ll text you when your table is ready. We were quoted for over an hour wait but it was much faster.
Boystown
Head out to Boystown, one of the U.S.’s best gay neighborhoods. Start the night out at Sidetracks, a very large gay bar with multiple bars, rooms, and even a rooftop deck. This was a great place to start the night, but they don’t really have a good dedicated dance floor so if you want to shake it, then pregame here and get moving onto somewhere else! We sorted of stumbled into Splash…well we heard Nicki Minaj was playing from the outside, so we had to go in. I really liked Splash on a Friday night, it’s a smaller bar with only one dance floor but the DJ that night was on-point all the way until they closed a little before 2 a.m..
Another place to go dancing is Scarlett Bar. It’s a small dance floor and bar but a great place to get down. On Sunday nights they do theme nights, we went on a Sunday as well and it was Beyonce night (can’t get much better than that)! But upcoming nights were Taylor Swift, Rihanna, and Katy Perry.
Day 3:
Take a long walk across the city, get those steps in because you will be eating a lot today!
Portillo's Hot Dogs
After sleeping in from the wild night in Chicago (some bars don’t close until 4 am) head to Portillo’s Hot Dogs for one of the best hangover recovery meals. You have to get the classic and Chicago-staple a Chicago Dog (includes mustard, relish, celery salt, freshly chopped onions, sliced ripe red tomatoes, kosher pickle and sport peppers piled onto a perfectly steamed poppy seed bun). Do you notice anything missing?! Where is the ketchup you might be asking? Ketchup is not allowed on a Chicago Dog; I’m not sure why, maybe it’s because there are already tomatoes, but keep that in mind when you’re ordering one! The Chicago Dog is really refreshing with all the vegetables and pickles topped on. While you’re there, you should also try one of their sandwiches, because their hotdogs are on the smaller side. We split a Combo Beef & Char-Grilled Italian Sausage sandwich with sweet and spicy peppers! Be sure to add the peppers too!!! Also, to top this all off an order of their crinkle-cut fries and two large beers (yes it was 11 am, but we’re on vacation)will hit the spot.
360 Chicago Observation Deck: Hancock Center
Take a nice stroll to the Hancock Center which features the 360 Observation Deck. We chose this observation deck instead of Sear’s Tower (Willis Tower) after countless recommendations from locals. Buy your tickets online (or use the City Pass) to skip the ticket sale lines (which can get extremely long). We waited around 15 minutes to get to the elevators to go up (the line would have been a lot faster, but they make you take a green screen photo before going up). The views from the Observation Deck are phenomenal! We went mid-day, but we also heard a great time is right before sunset so that you can see daytime views, sunset views, and then the city lights. There is also a nice bar with reasonably priced drinks (for a tourist site in Chicago). We grabbed a glass of champagne, a comfy seat, and just enjoyed the views. There are also interactive maps that can help you explore the city.
Scooped Cookie Dough Bar
Who doesn’t love cookie dough? Well, how about a cookie dough bar?! Yes, paradise does exist! Scooped has a variety of cookie dough flavors and some toppings to enjoy. The flavors we enjoyed the most were the Monster and Chocolate Chip. The flavors are very rich so sharing two scoops between two people is probably the way to go!
Bad Hunter
Bad Hunter is a beautifully decorated bar and restaurant with lots of natural light. We stopped in for drinks, but they have a heavily vegetarian influenced menu that looked delicious. The cocktails are very intricate and unique…to be honest, I didn’t know what 90% of the ingredients were but they still turned out well!
Bar Siena
We stopped in Bar Siena, another restaurant and bar. The food menu looked great, but we were still on the liquid diet, so we grabbed some wine and beers. The decor is cool with a very intricate centerpiece above the main bar. They have TVs with most of the games on too.
Parlor Pizza Bar
West Loop
Continue the pizza tour of Chicago with Parlor Pizza! Even though it’s a large restaurant, be sure to make a reservation in advance as this place gets packed! It’s not Chicago Deep Dish Pizza, but it is still worthy of a stop in Chicago! We ordered the Great Balls of Fire (a spicy meat lovers pizza), the Burratta Be Kidding Me, and finally the Save the Last Ranch (yes a pizza made with ranch!!!). With great names like these, our expectations were extremely high. Our expectations were met and then some because every pizza was fantastic. I would strongly recommend the Great Balls of Fire! They also have some very interesting desserts like the dessert taco, but because we were so full, we didn’t get the chance to try any.
RM Champagne Salon
The RM Champagne Salon is a hidden gem down a tiny alleyway that most people would easily walk past. With comfortable outdoor seating, a beautifully decorated inside, and wonderful full-service bar this is another must-do on your Chicago trip!
Day 4:
The last day in Chicago! Explore as much as you can before your flight in the evening.
Duck Duck Goat
To be fair, we wanted to try Girl and the Goat, but it is impossible to get a reservation, so we “settled” for Duck Duck Goat…which I wouldn’t even call it settling because it was so darn good! Duck Duck Goat is a dim sum fusion themed restaurant. It’s a perfect brunch spot and fills up quickly so be sure to make a reservation. We enjoyed the Goat and Duck Springroll, the Jiaozi, beef wonton soup, beef slap noodles, scallion pancakes, and the crunchy tasty messy wings. This was a lot of food for two people, but we braved through all the delicious flavors. My personal favorites were the beef slap noodles and the crunchy tasty messy wings. They also have Boozy Bubble Tea (yes, dreams do come true). I ordered the Give It a Chai (they’re so clever in Chicago with naming food and drinks) which was whiskey, chai, sweet cream, and cold brew.
Art Institute of Chicago
Even if you’re not a big art fan, the Art Institute of Chicago is fascinating and has something for everyone. One of their most famous paintings is the American Gothic painting (the one with husband holding a pitchfork standing next to his wife). There is a lot to see, and you could spend the whole day going through each exhibit. Some of my favorites were the modern art and textiles. The tickets are a bit expensive but buy yours online to skip the long lines. If you need a refresher, there are a few bars, coffee shops, and even a full cafeteria.
Devil Dawgs on State
After enjoying all the world famous art, treat yourself to another Chicago Dog at Devil Dawgs on State. A hole in the wall restaurant with a variety of hotdogs including the Taco Dawg which is basically what it sounds like (taco toppings on a delicious hot dog). My favorite though was the original Chicago Dawg and their fries (which are enough to split between two people).
Cindy's
They call it the grand jewel sitting atop the Chicago Athletic Association Hotel. There is a good reason for this because it is so unbelievably beautiful. With glass ceilings and tons of great natural lighting, decor to die for, and a balcony with breath-taking views of Chicago, it is easily my favorite bar in this city. The Chicago Athletic Association Hotel that houses Cindy’s is beautiful on the inside as well.
Pequod's Pizza
Finish off the night with the perfect Chicago’s Deep Dish Pizza. Pequod’s is a locals favorite and not normally mentioned with the big 3. It’s small, takes about 3 hours until you get your pizza, but it’s completely worth it. There are a few ways you could do this; I think the most simple way is to order pick up and eat it back at your hotel room or in the park. If not, then you’ll end up like us waiting two hours for a table. They give you a buzzer, so you need to stay close, unfortunately, but we went to Devour 312 and grabbed drinks/appetizers before. They had great food and good drinks (including their chicken sliders). Then once we were seated, we ordered our pizza and was told it would take around 1 hour and 15 minutes. It took that much time, which we thought they were just quoting a bit higher. Even with all this wait time, the pizza was 100% worth it. We ordered a medium with extra cheese, extra sauce, pepperoni, sausage, mushroom, and olives. The extra sauce and extra cheese were a good idea (even though it takes longer to make)! I would strongly recommend this place, as I felt like we got a real authentic experience.
Tips and Tricks:
- Chicago is one of the more expensive cities we have visited, especially if you do stay downtown.
- For the best time to visit: the winters are a bit harsh, so most people recommend visiting in the summertime.
- Getting Around: Ubers and Lyfts were generally easy to get, but there are a lot of issues with GPS on smartphones in the downtown area so this can make it harder for Ubers to get to you (and when we were walking around using Google Maps).
- Some other tourist tips: We were told to avoid Navy Pier as it’s very touristy. We didn’t get the chance to visit Wrigleyville (the area around Wrigley Stadium), but it’s supposed to be a great neighborhood. Another place, we didn’t get to check out because it was a little further north is the famous Green Mill Jazz Bar.
- Check out more of our favorite itineraries for Chicago here!
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It is sooo beautiful! Seriously never even considered going there before, and now it’s on my list!
Thank you! Let us know if you have any questions. We’d love to help you plan your adventure.
Love your photos! Planning a trip in February and I’m even more excited now. Thank you.
We hope you had a great time. Thank you for the kind comment.