Affordable 5-Day Summer Chicago Itinerary

They said that Chicago in the summertime is the best, so I wanted to visit Chicago and check it out for myself. Verdict: they’re not wrong! In this blog post, I’ve included the exact 5-day itinerary that we used in order to keep this trip affordable. If you haven’t been to Chicago — and even if you already have — check out this blog post to plan your next visit! If you make it to the bottom, you’ll see the total amount that we spent per person. I wonder if it’ll surprise you.

Day 1: Rooftop Bar, Damen/Wicker Park, and Downtown Walking Tour

Land in Chicago (either at O’Hare or Chicago Midway) and get a Ventra Card and put a 7-day unlimited pass on it. This way, you could save a ton of money by using Chicago’s extensive transit system, colloquially called the “El” (this is because the original train lines are elevated, though some lines are now underground).
Depending on the time of day you land, you may be able to go directly to your hotel/Airbnb and check-in
- We landed at 8am, so we had lots of time to kill before we could check into our Airbnb. Luckily, they offered bag storage and we were able to use the lobby bathroom, freshen up, and lock up our suitcase.
After you settle into your accommodation, hop on the El and head over to the Damen station off of the Blue line.
At this point, you may be hungry; luckily, there are a variety of restaurants around the station to choose from. We had an early lunch at Dove’s Luncheonette, a Tex-Mex restaurant set in an old, retro diner. Our table was in their sidewalk patio and it was a pleasant experience!
After lunch, walk to the Robey Hotel and take the elevators to their Rooftop, called the Cabana Club. Entry is free, but they do require a $15USD minimum spend per-person. They had frozen drinks that were $15 each, so that covered our minimum.
- The rooftop is a bit small, but the views from the Cabana Club were unmatched.
After you relax with a drink at the Robey’s Cabana Club, it’s time to explore the cool and eclectic neighborhood of Wicker Park. Walk down N Milwaukee Ave, which is the main thoroughfare through Wicker Park. We walked the stretch from the Damen station to the Division station.
- Wicker Park has historically been a gathering place for the alternative counter-culture in Chicago. Though the area seems to have been impacted by new-wave gentrification (for instance, there are national chain locations like Sweetgreen and Jeni’s ice cream in the neighborhood), there are still a number of shops, boutiques, and restaurants that have preserved its eccentric origins.
Stop into the Myopic Used Bookstore on N Milwaukee. It was a gem! There are other cool thrift stores we saw for those who like thrifting.
At this point, you may need to take a quick break to rest (we sure did…plus it was time for us to check into the Airbnb)
Next, take an Architecture and History Walking Tour of Chicago (click the link). I booked this tour through Airbnb Experiences and our host, Kelly, was fantastic. It’s an affordable tour with a price tag of $29USD per person.
- This particular tour took us through downtown, along the river front, and it included snacks. We not only learned about Chicago’s history and its architecture, but we also learned some cool fun facts about the city.
After the tour, it’ll be around dinner time. Grab a classic Chicago hotdog at Portillos (plan-based hot dog is available).
After dinner, the night is yours! You may consider walking along the riverside at night.

Day 2: Beach Day, Chicago Pizza, and Evening at Navy Pier

The first half of the day will be spent at one of Chicago’s famous beaches! Chicago has a long coastline along Lake Michigan and most of the beaches (if not all…I’ll have to fact-check this) are open to the public.
There are a number of beaches to choose from, but we chose North Avenue Beach and it did not disappoint. I couldn’t believe how clear and blue the lake was. It actually looked like a beach in South Florida!
Bring your towels, sunglasses, a book, and plenty of water, because you’ll need it for a hot summer day in Chicago! At North Avenue Beach, there was a vendor renting out umbrellas and lounge chairs.
- We rented an umbrella for $25USD for our entire stay; it was a good decision because we would’ve otherwise melted under the sun.
If you want a snack or an early lunch, there’s a restaurant on the beach called Castaways. The cool part is that the restaurant is housed on an old ship!
After a few hours at the beach, you can head back to your accommodation to shower and freshen up, or you can head straight to the next part of the itinerary. The choice is yours!
Next, you’ll head over to Navy Pier. Navy Pier is a multi-entertainment, retail, and commercial district that sits on top of — you guessed it — a pier. When we were there, we saw a mix of locals and tourists. Navy Pier includes a large ferris wheel and other rides, multiple restaurants and food courts, a hotel, performance venues, and retailers.
- Have dinner at the Giordano’s location at Navy Pier. You can’t go to Chicago and not have Chicago-style deep dish (though I wasn’t personally a fan, I think everyone should try it out for themselves)
- Head on some of the rides. You can buy tickets from kiosks on-site or online in advance (which is what I did).
If you’e at Navy Pier on a Wednesday or Sunday night from Memorial Day to Labor Day, don’t miss out on the fireworks show.
Enjoy your night at Navy Pier and then head back to your hotel or Airbnb for some much-needed rest. The rest of the night is yours.

Day 3: Millennium Park, Institute of Art, and Dinner on the River

It’s time to get up bright and early, because you’ll be heading to Millennium Park to see “The Bean!”
- One of Chicago’s most iconic landmarks is a permanent sculpture called Cloud Gate, but it’s colloquially known as “The Bean” since it resembles — you know, a gargantuan bean. The artist, Anish Kapoor, has said that the sculpture was inspired by liquid mercury.
- In order to avoid the droves of tourists, it’s best to visit as early in the morning as you can. We got there around 10am, and though there were groups of people present, it wasn’t as packed as later in the afternoon.
Enjoy your time at the Bean. Take photos and videos and check out how the sculpture reflects the landscape around you. Don’t forget to go underneath the sculpture, too!
After you get your flicks at the Bean, you may be hungry for breakfast. Walk a block north to Stan’s Doughnuts, located at 181 N Michigan Ave. Stan’s Doughnuts is a beloved Illinois institution which offers speciality doughnuts, coffee, and an all-day breakfast menu. There are even vegan and gluten-free options. I love a speciality doughnut shop and Stan’s Doughnuts didn’t disappoint.
After breakfast, you’ll walk back down through Millennium Park to head to the Art Institute of Chicago. This museum is the premier center for fine art in Chicago. If you’ve ever been to the Met in NYC, this museum reminded me of it. You can easily spend hours in this place. Good thing you just had some food and coffee!
- You can purchase tickets as walk-ups, but I booked in advance in order to skip the ticket line.
- If you have backpacks (like we did) or other large bags, you’ll have to check them in (but it’s free!)
Once you’ve spent the afternoon at the Art Institute, you’ll spend a little bit of time exploring Millennium Park (the sun should be a little softer since it’s early in the evening). Millennium Park is a large public green space right in the heart of “the loop” of Chicago. The park is pretty massive and has different sections to it. Here are a few areas you can check out (it’s all FREEEE):
- Lurie Garden
- Maggie Daley Park (great for kids)
- Jay Pritzker Pavilion (there are lots of free shows here in the summer)
After you spent about an hour walking around the park and enjoying greenery, you may be ready for another meal. Walk (or bike, by using the Divvy bikes) north towards the riverwalk and have an early dinner at Pizzeria Portofino. Pizzeria Portofino is a sleek, modern river-side restaurant that serves up coastal Italian cuisine and brick oven pizzas. Get a patio table, if you can!
- We met some friends at this restaurant and had a lovely experience. The menu, service, and atmosphere was fantastic. Order the king crab and artichoke pizza and a Portifino Spritz!
After your dinner, if you have the energy, you can catch a comedy show at Laugh Factory Chicago. Our entry was free by rsvp’ing on their Eventbrite, but there is a two drink minimum purchase per person.

Day 4: Pilsen and the West Loop

Sleep in and rest from all of the activity you’ve been doing. You’ll spend the day exploring two different neighborhoods in Chicago: Pilsen and the West Loop
Once you’re up and ready to explore, hop on the “El” and go to Rubi’s on 18th St. Pilsen is the heart of the Mexican community in Chicago, known as “Little Mexico.” Did you know that Chicago has the 3rd largest diaspora of Mexicans? I sure didn’t.
- The tacos at Rubi’s were sublime. There are meat and vegetarian/vegan options. I still think about those tacos weeks later!
After you’ve had lunch, you’ll walk over to the National Museum of Mexican Art. During your walk, enjoy all of the street art that Pilsen has to offer (it reminded me of Wynwood, Miami, but in Chicago)
Arrive at the National Museum of Mexican Art, where admission is always free.
- This museum showcases art from Mexican and Mexican-American artists, but they also provide a lot of information about Mexican history, culture, and heritage.
- There’s one permanent collection, and during our visit, there were two different exhibitions about Frida Kahlo (they were awesome!)
After you’ve spent a couple hours at the museum, walk to the park next door and spend some time relaxing. There’s a fantastic view of the Willis Tower from this park.
Next, you’ll hop back on the “EL” on the pink line to head to the West Loop. The West Loop was an industrial area that was re-developed to one of the Chicago’s trendiest, young neighborhoods (it reminded me a bit of West Village and Chelsea, Manhattan).
Once in the West Loop, you’ll walk around Fulton Market, which is not a singular market, but actually a mixed-use district of retail, residences, offices, and restaurants housed in old warehouses. Take a look inside the different establishments.
At this point, you may be ready to eat again. The West Loop is known as a foodie haven as there are a number of highly-rated and popular restaurants in the area.
1. We personally kept it simple and went to the Time Out Market Chicago, where there’s a food hall with many different options. This Time Out Market also included rooftop seating.
2. I heard that the restaurant Au Cheval is a fan favorite.
Save some room for dessert! After dinner, head to BomboBar for some massive, Instagrammable shakes (or gelato or dougnuts, if extravagant milkshakes aren’t your thing)
After dessert, spend your last night in Chicago by renting a Divvy bike (Chicago’s bicycle sharing system) and biking south along the Lakefront Trail. You’ll get a great view of the skyline when it’s dark. And don’t worry too much about safety; when we did this, there were still lots of bikers and pedestrians on the trail after dark, and the trail is lit.

Day 5: Hyde Park then Head Home

If your flight back home is in the morning, then you’ll have to pretty much head straight to the airport after checking-out of your accommodation. But if your flight is in the late afternoon or night, then you can use part of the day to head south and check out the historical neighborhood of Hyde Park.
After storing your bags, take public transit down to the Southside to the 53rd street corridor. You can walk down 53rd St and grab lunch or breakfast from one of the street’s numerous restaurants. You can also pop in to any shops if they pique tour interest.
Hyde Park is home to the University of Chicago campus. After walking down 53rd St, feel free to head over to UChicago’s campus and appreciate its amazing architecture.
If you have time, you can also check out the Frederick C. Robie House, the Museum of Science and Industry, the DuSable Black History Museum, or stroll through Jackson Park.
After that, grab your bags and head over to the airport. Have a safe journey home!

How much did our trip Cost?

Including flights, Airbnb, tickets, activities, transit, and food, our trip came up to $716 USD per person. Not bad for a 5-day trip to a major city in the United States!