weekend guide

chicago, il.

This might very well make one of us, but I think Chicago is the perfect stress-free weekend getaway for people living in the continental US.

First, it’s centrally located. Pretty easy to get to no matter where you’re coming from. Flights are aplenty and generally not overly expensive.

Second, there’s plenty to do without having to plan. It’s just another big city. Except cleaner and less claustrophobic. You eat, shop, drink, maybe hit a museum or four, an observation deck or two, snap a few pictures in front of a glossy bean and call it a trip. It’s easy to fill a couple days itinerary in downtown alone, and truly very little planning needed.

Third, it’s the midwest. People are nice. People will go out of their way to help give you directions, take a photo for you, tell you about their favorite bar. The people of Chicago are friendly (especially compared to coastal people), which makes for again, an easy domestic trip.

But then again, the weather is almost always bad, so maybe Chicago isn’t that ideal. But on its good days, it’s great. Great enough to make you forget about the bad. 

So here’s how I’d spend a weekend in Chicago. Friday evening to Sunday afternoon, 36 hours style. And some thoughts on first time vs more familiar visitors. The general idea is to get a good mix of (actually good) touristy sights and some more “local” spots to get a better sense of the city, a format that is easily repeatable for short trips with family, friends or solo. And of course prioritizing places that are fairly central and easy to get around.


Unless you are already in the Midwest, you’re probably going to be flying into the city. And you generally have two options: O’Hare and Midway. The former being the bigger international airport (a la JFK in NYC) located about an hour north west of downtown), and the latter being the smaller more local airport (a la LGA in NYC) located southwest of the city.

Either way, once you fly in, it’s pretty easy to get into the city via public transit. O’Hare is connected by the Blue line and Midway by the Orange line. While the CTA isn’t the fastest or most reliable metro system around, it is worth taking if you’re coming in during rush hour and if you’re headed downtown (which, for a short trip, you likely should be), as traffic in and out of the city can be pretty brutal with all the commuters.

when to go

Let’s be honest, Chicago has bad weather, all year round. It’s either too cold or too hot, pouring rain, storming, thick with humidity, etc. Generally the safest time to visit is between Memorial Day and Thanksgiving (which spans a generally chilly but tolerably so late May/early June, a sweaty July and August, a lovely September, and a chilly fall that is more than tolerable because you can do fall shit in fall attire which makes up for the lower temperatures). If you don’t mind colder weather, it’s also real cute during the holidays. But the dead of winter is miserable for everyone.


For ease of transportation (both in/out of the city and within), your best bet would be to pick one of the many many hotels located in River North, the Loop or West Loop. I have a bias towards River North and West Loop – you get much better food options than in the Loop. But transportation wise, the Loop does offer the most accessibility without having to transfer. Pretty much any hotel chain you can think of will have a location in downtown Chicago, but here are some favorites:

  • $ – Freehand (River North), Found Hotel (River North)
  • $$ – Swissotel (Loop), Virgin Hotel (Loop), The Godfrey (River North), Pendry Hotel (Loop)
  • $$$ – The Hoxton (West Loop), Ace Hotel (West Loop), LondonHouse (Loop), Viceroy (River North)

Literally just walking along the river on a nice day is entertainment.

During summer nights, they project films on the facade of the Merchandise Mart.

things to do

For a first time visitor, I’d recommend spending one day hitting all the main sights downtown, and the other day picking a neighborhood to explore so you can get a better sense of the city (aka a safe distance away from Michigan Ave), but still keeping ease of access in mind given the shorter time frame.

For visitors that have already done the touristy things, I still recommend spending one day downtown and another somewhere else (perhaps a new neighborhood you’ve never been to?). But the best part is you can pick and choose just the parts of downtown you like (my suggestions below).

DAY ONE | dinner & late night music entertainment

So it’s your first night in the second city, the greatest hits all ahead of you. You’re tired, hungry, slightly disoriented. What’s for dinner? Pizza? No. Save that for tomorrow. Opt for something easy, accessible. Something that doesn’t involve too much waiting. Somewhere you can roll into without even needing to freshen up at the hotel. 

Burgers. You’re getting burgers and boozy milkshakes at Small Cheval. Low hanging fruit? Sure. But isn’t guaranteed satisfaction exactly what you need for the first meal after you land in a new place? Plus they have several locations around the city. 

Perhaps it’s not your first time here, you’re familiar with the food scene and you’re looking for a solid dinner to kick off your trip. Honestly Small Cheval still isn’t a bad choice if you don’t want to have to think. But if you’re feeling fancy and want a bit more of a sit down type of dinner, but still with comfort food. Stay within the Hogsalt family and make a reservation at Au Cheval in West Loop for some elevated diner-inspired dishes. Or perhaps you do want a burger, but leveled up. The Loyalist has one of the best in the city. The casual brasserie-style restaurant and bar offers a more approachable neighborhood feel to its Michelin award-winning sister restaurant upstairs. 

Then hit up a jazz club or blues speakeasy. Preferably one closer to your hotel (several options in River North and the Loop – ie Howl at the Moon, Buddy Guy’s Legends), because you will want to be up early. 

DAY TWO | for first time visitors


Wake up, put on some comfy shoes and try to head out early. If you need motivation here it is: donuts and a boat ride. Hear me out: The play here is to make your rounds for the city’s best donuts and coffee and then board a boat to see the city over breakfast.

First up, the donut tour. Chicago loves its donuts, and luckily most of the local chains have locations within a few blocks of each other conveniently  a short walk from where most boat tours start.

Head over to River North, and depending on how ambitious you are, hit up at least one of the following. 

Doughnut Vault | literally a hole-in-wall, serving up a daily selection of fresh old fashioned doughnuts until sold out. They only have two locations in the city, but also show up at other Hogsalt establishments.

Firecakes | a longtime local donut shop, with a premium selection of craft donuts (aka firecakes) of yeasted and buttermilk old fashioned kinds, and fancy seasonal specials .

Stan’s Donuts | an LA (specifically Westwood) import that has grown to be an ostentatious chain in downtown Chicago with a wide variety of donuts spanning classic flavors and more creative forms.

Do-Rite | some places do chicken and waffles. Do-Rite does chicken and donuts. Their buttermilk old fashioned donuts give all the others a run for their money, but if you’re craving something savory, go ahead and grab a sandwich too. Think of it as a special guest to this donut tour.

Then, boat tour.

There are a few different routes and options throughout the day but most of the main boat tours run about 90 minutes and take you around the Loop and into Lake Michigan for an unobstructed view of the city’s historic and new architecture. Tickets are $40 for adults, $18 for children, and can be pre-booked (recommended for high season weekends) or purchased at the window by the river. A boat tour may seem like a tourist trap, but this one is actually well worth the time. Chicago is a city best viewed from the water that conveniently snakes through and around the skyscrapers. It’s the kind of attraction that locals don’t mind doing once in a while. You get your views, you get your historic tidbits about the city, you get some time to sit back and relax and watch the city go by. It’s a win-win-win.


While you’re already by the river, take a walk along Riverwalk and admire the city and its many bridges. Skip the riverside restaurants and bars and grab a classic Chicago hotdog at Portillo’s in River North. Or just grab a Chicago-style hotdog from a vendor and enjoy it with a view by the river. Or walk up the other side of the river and take your pick of some of Chicago’s most popular bites at a food hall like Urbanspace or Revival



Then, walk around the Loop, hitting the main landmarks and public art pieces before walking over to Millennium Park for an obligatory photo by Cloud Gate. Continue your walk through Grant Park, admiring the glorious Buckingham Fountain and continuing down to Museum Campus.

Take your pick of the three. The Field Museum of Natural History is a family favorite. Home of Sue the t-rex, and often hosting interactive special exhibitions. The Adler Planetarium is worth walking out to just for the view back at the city, as it juts out into Lake Michigan. Also great for catching a nice show where you can just basically use it as an excuse lay down in a comfortable temperature regardless of how interested you are in outer space. And then there is Shedd Aquarium, for those more interested in the deep sea. 

After you’re done with the museums, catch the red line (or the many buses running along Michigan Ave) back up to River North/Streeterville. If you’re with kids, stop by Navy Pier. If not, just go to Milton Lee Olive Park for the views of the northern city and beaches along the shore.


Walk back toward Michigan Ave and do some shopping. Sure, most of the shops are major retailers, but there’s just something more… magnificent about shopping on Michigan Ave (especially leading up to the holidays when it’s all cute and decorated). Do what you need to do – go to the Water Tower (and Water Tower Place), stop by the giant Starbucks Roastery, buy some Garrett’s Popcorn. Maybe skip the horse-drawn carriages though, that one is definitely a tourist trap. 

And then for dinner, pizza. Listen, I get that a lot of people have weirdly strong opinions about sauced up flat bread, but regardless of whether Chicago’s signature deep dish can be called a pizza or a pie, when you’re in a new place, you gotta give the local delicacy a shot. And lucky for you, there are several options that are extremely accessible downtown. Namely Lou Malnati’s, Giordano’s and Uno. So pick your poison. Either way, try to make a reservation or if reservations aren’t available, put a name down and order in as these pies take a while to get going. They aren’t the most exquisite dining experiences but they are family friendly and do the job. If you’re really invested in local deep dish, grab a car to Pequod’s in Lincoln Park. Or, if you are adamantly against Chicago’s favorite form of pie, Eataly in River North (right next to Uno!) is a reliable choice (and though popular, it is its own building, making it superior to the locations in NYC and LA).

And if, for some reason, pizza really isn’t your thing, you can still have a quintessential Chicago experience by heading up to one of the Gold Coast steakhouses. The Gibson, Hugo’s Frog Bar, Carmine’s, Maple and Ash. If it looks like a scene but you can’t quite place the clientele, you’re at the right place. 


Then get some post-dinner drinks at the Signature Lounge. Chicago has no shortage of rooftop bars, but if you’re here to be a tourist, the view from the 96th floor of the John Hancock tower is hard to beat. Sure the drinks are pricey and there is often a wait. But we’re here for the Chicago skyline, not for the drinks. If you’re feeling like a splurge and want more of a peaceful atmosphere to enjoy the view, they also have a restaurant on the 95th floor.

Or, you could very well flip it and do some sunset drinks up at Signature Lounge and then grab dinner afterwards.

DAY TWO | for repeat visitors


Get your morning coffee and walk around Millennium Park before the tourists settle in. Yes, this place is actually lovely in the mornings. Walk through Maggie Daley Park and Lurie Garden. Pop into the Chicago Cultural Center to see what’s happening. 


Loop: Hero Coffee, Heritage, Intelligentsia, Two Zero Three, Fairground

River North: Umbria, Heritage, Foxtrot, Cafe Integral

Then it’s time for brunch. Take the red line (or any of the many buses that run along Michigan Ave or Clark St) up to Gold Coast. Well before the sugar daddies start settling into their tables at the usual haunts, Gold Coast is a pleasant and beautiful neighborhood to walk through. For a more casual (and pastry-forward) European meal, go to Hendrickx. For a more decadent sit-down experience, go to 3 Arts Club at Restoration Hardware. Make sure you go up to the roof while you’re there.

After brunch, walk a few blocks north to Lincoln Park. Walk off the carbs, catch some views of the city, maybe say hello to some of the animals and then grab a Divvy bike and ride along Lakeshore, the scenic route.


Hit a museum. Pick your favorite, or try a new one. If you’re here with kids, Field Museum is always a good choice. If you want a traditional art experience carve out a good few hours for the Art Institute. For a more casual contemporary art experience that won’t require wading through tourists, go to the MCA in River North. They often host touring exhibitions on the top floor, and it’s generally less crowded here than in other cities.  

Catch a show. Local theatre groups, touring Broadway musicals, and of course comedy. Many of the theaters are in the Loop. Choose your preferred form of culture consumption for the afternoon.


For dinner we’re headed to West Loop. West Randolph St, with some of the most popular food destinations in the city. Some of the most influential hospitality groups have several concepts in the neighborhood If you can snag a reservation early enough, go to one of the Goats (or other Boka Group restaurants that dominate the neighborhood). Or, opt for one of the One Off Group at The Publican or Avec. Or maybe it’s Hogsalt: basement ramen at High Five, casual barbecue at Green Street Smoked Meats. Or maybe it’s leaning into international cuisines: Indian at ROOH, Peruvian at Cabra, Japanese at Momotaro. Point is, we’re eating well tonight.

For dessert, get some bombolones and gelato at Bombobar

And then finish off the night with rooftop drinks at Cindy’s. Yes, very much a scene, but hey, you’re a visitor, and what better excuse to drink to that quintessential view?

DAY THREE | choose your own adventure

For your final day, choose a neighborhood to explore. One that is easy to get to from downtown, and easy for transit to the airport. 

For first time visitors, Lincoln Park is an easy one. Close enough to walk to (but don’t – take a bus or train or car and save yourself the 30 minutes). A little spread out but very picturesque. And a great way to spend a more low key day to wind down for the weekend.

Sample Itinerary:

  • Take the brown or purple line to Armitage. Get brunch at one of the many brunchy restaurants on Halsted, and then spend some time browsing the shops in the area.
  • Brunch Options:
    • Cafe Ba Ba Reeba – brunch tapas and Spanish-driven menu
    • Summer House Santa Monica – classic Californian brunch staples
    • Blue Door Farm Stand – fresh local ingredient-driven
    • Willow Room – more low key New American spot
  • Head east over to Lincoln Park. Spend the afternoon walking through the park. Go through the zoo, bike along the shore, lay out on the beach, see the Peggy Notebaert Nature Museum. Maybe grab some snacks and drinks and have a little picnic by the Conservatory. Walk through the picturesque boardwalk and marvel at the view beyond.

For repeat visitors, Wicker Park and Logan Square always have fun things to offer. Plus, it’s right on the blue line, making it an easy trip to O’Hare. 

Sample Itinerary:

  • Grab some morning coffee at Ipsento and then walk or bike the 606.
  • In the summers, stop by the open street festivals in Wicker Park that often take over Milwaukee on the weekends. Or go to the Sunday Logan Square farmers market.
  • Grab some lunch at one of the many great restaurants in the area.
    • In Wicker Park/Bucktown: etta, Mott St, Ina Mae Tavern, Mindy’s
    • In Logan Square: Lula, Cellar Door, Noodlebird (Fat Rice), Paulie Gee’s, Serai
  • Shop around the many boutiques, art gift shops, book stores and thrift shops along Milkwaukee Ave. Some standouts: Myopic Books, Saint Alfred, Una Mae’s, Bow & Arrow Collection, City Lit Books, Fleur, Monarch.
  • Get an afternoon pick me up before heading out. Taste some of Chicago’s best pies at Bang Bang Pie & Biscuits (with a great outdoor seating area too). Or, cool down with some iced chai (and perhaps some Nepalese treats) at Chiya Chai. Or wind down your weekend at a local brewery — there’s no shortage in this part of town. Revolution Brewing is one of the biggest, Piece is also popular (and serves pizza, which never hurts). Middle Brow, Pilot Project and Hopewell are other solid options in the area.

And then you leave wanting more, ready to plan another weekend in the city.


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