Chicago a.k.a Chi-town a.k.a the windy city, makes you fall in love with its architecture, vibes, views, and if you are lucky enough the weather! Summer of Chicago is what a dream city would be like. But, don’t get too excited because you can see all the seasons over a weekend, only in Chicago. Yeah, our visit to Chicago made us understand why Chicago has all the weather memes to its credit. but, on an excellent sunny/ clear day in Chicago, this city makes you fall in love with itself.

The weather aside, let’s talk about all the amazing things Chicago offers. The infamous Chicago Skyline, restaurants and bars- by the river, showing off the skyline, rooftops with amazing views of the city, the architecture and history, and the museums. Let’s dive into the must-do and must-eat list in Chicago.

For recommendations on top things to do on your first trip to Chicago check the blog post – ‘Chicago things to do for First-time visitors’ here!

My FAV Bars with a view or a twist!

Chicago downtown has so many sights that could take your heart away. They really have made the best use of the beautiful views from these rooftop bars and riverside restaurants. The variety in the bar and restaurant culture here is unlike any other place. There is definitely a place for everyone in this town. Now without further ado let’s dive into the ones that you should definitely try

1. Cindy’s Rooftop

This rooftop restaurant and bar opens up to one of the best views of the city. Right opposite millennium park the rooftop faces the Bean, the Park, and the amazing skyline of Chi-Town! A visit to this place is a must when visiting. Their cocktails are so on point! and after a long walk by Millennium Park, this makes a perfect spot for a drink or two with a view. Even if they do not have a table, the rooftop views are a treat to the eyes while enjoying your drinks!

View of the bean from Cindy’s Rooftop
2. London House

Another gem in downtown by the Chicago River is the rooftop at London House. Great views of many high skyline buildings from the top of the 22nd floor, make it a perfect place to hydrate yourself on a hot summer evening. Do not forget to get a reservation here, as it is pretty booked all the time. Since we were in-house guests we got the reservation last minute as well but it usually gets booked out quickly.

3. Aba Rooftop Lounge and Restaurant

A view of the Willis a.k.a. Seers Tower and an amazing selection of food, desserts, and drinks. It is a perfect place to enjoy with a group of friends or for a nice dinner out. On the fancier side, I highly recommend getting a reservation here before coming. You have to try their Creme Brulee Pie, it is to die for!

4. Federales

Located on the West Loop, this bar is famous for its tequila shots in ice glasses and then throwing those empty ice glasses at the bell to make it ring. This bar has a super cool vibe like none other! They serve Mexican food and amazing drinks. You have to visit here once to Ring the Bell, on its outdoor patio. A one of a kind of challenge, where people take a shot and attempt to throw their ice shot glass on the target while the whole bar watches. It does get crowded and reservations are recommended!

The Famous bell challenge at Federales
5. City Winery Riverwalk

Another way to live life Chicago-style is to visit the City Winery by the riverwalk. This place opens only during the summer months and offers a super chill vibe by the Chicago River. The seating on the tables is first come first serve basis, but the real feel is by grabbing a drink and sitting by the steps near the Chicago River while enjoying the views and architecture. And if you want more style you could even arrive by your boat and dock here for some drinks and fun! To know more about when it is open for the season visit here.

6. Cloud Bar at 360 Chicago

Enjoy a drink with a view. And what better view of Chicago than from the 94th floor looking out to the Chicago skyline? The observation deck at John Hancock Center is the perfect place to sip a cocktail while you enjoy the expansive Chi-Town from the top. A trip to JOhn Hancock is a must and having a drink from this view is the cherry on top!

Food Favs not to Miss when in Chicago

1. Ramen San

Sometimes, I wonder if Ramen thinks about me too. Take me back, because Ramen 🤤. You can’t miss this when in Chi-Town! The best ramen ever..! I would highly recommend trying their: Vegetarian Ramen, Gyoza, Mantou Buns, Dumplings, Sake Bomb Yuzu, and some Matcha Puff! Be prepared to wait if you go during lunch or dinner times. Reservations recommended!

2. Beatnik by the River

Another amazing restaurant with a breathtaking view! When you are entering the restaurant you can’t imagine it leading to a section where you could dine by the river. The drinks, food, ambience everything is on point. I would highly recommend a visit here and sitting by the river while enjoying your meal.

3. Pizza Portofino

A walk by the Riverwalk and you can spot this restaurant almost full all the time, especially during the summer months. Amazing food, and desserts and love the outdoor patio. Loved their Hazelnut White Chocolate Mousse which was highly recommended and lived up to its expectations.

4. Beatrix

A perfect spot for breakfast, offering a great variety of options. The food was so presentable and tasty at the same time. It is very popular so I do recommend reservations ahead, especially on weekends.

5. Lou Malnati’s and Giordano’s for Chicago-style deep-dish pizza

And no trip to Chi-town is complete without the Deep Dish pizza. Yes, it is a must!! famously there are 2 main spots to try out deep-dish pizza: Lou Malnati’s and Giordano’s. Make sure to go to one of these to try the famous pizza. We tried Lou Malnatis, I enjoyed it while I ate it. But it is not for a weak stomach like mine. I had a bad stomach ache later but it could just be because of all the butter and the heavy crust! Irrespective I wanted to try it I did, but I would always prefer the traditional pizza over it!

6. Labriola

Another gem by the Michigan Ave. Amazing Italian food. Loved their pizza and pasta. I like this better than the deep dish definitely. Just loved their crust, so crispy and crunchy.

7. Chiya Chai

If you know an Indian, you know we take are Chai (tea) very seriously! And this place proves it. Amazing variety of tea which was perfect fro the chilly Chicago weather. Their snacks are a must-try as well. Perfect combinations with a hot cup of tea!

8. Pappa Roti

A different kind of Bun Dessert, which is a must-try on your visit to Chicago. Super soft and perfectly sweet, with a variety of flavors to add. They serve the Buns and coffee. The wait might be long but while exploring Chi-town, this made a perfect spot to relax and enjoy a bun with some drink.

9. Harolds Chicken

Another Iconic spot to eat in Chicago would be Harold’s Fried Chicken. They are famous for their fried chicken with their sweet-and-spicy sauce. Harold’s Chicken Shack (also referred to as The Fried Chicken King, Harold’s Chicken, or simply Harold’s) originated in Chicago in 1950’s. It is a favourite among locals!

For other recommendations on what to do on your trip to Chicago check out the post titled: “Chicago things to do for First-time visitors” here.