If you're flying in, Chicago has two airports, O'Hare and Midway. Both are fine to fly in and out of and relatively accessible- Midway is smaller and in the city, O'Hare is larger and at the edge. Both are connected to downtown by L trains which take a little less than an hour, or are a 25–60 minute drive depending on traffic. Cabs and rideshares are usually easy to get both places.
If you're flying in, we'd recommend against a rental car unless you're planning to go to and from the suburbs or outer neighborhoods. The money you would pay for the rental and parking will go a long way towards other ways of getting around like Uber/Lyft, CTA tickets, or Divvy Bikes, and it will be much less hassle. If you stay downtown, a number of the things you'll want to do will likely be walkable.
If you're a hotel fan and want to keep it super simple, here are a few options where we have blocks or discounts:
A modern River North hotel with its own contemporary art gallery. A little over 2 miles east of our venue.
A massive, recently renovated Hyatt right on the river. Similar distance to venue as 21c and close enough to meet up with people staying there.
For those looking to splurge, a trendy Fulton Market hotel with great food both in the hotel and nearby. Closest to our venue but would still be about a 30 minute walk to get there.
If you'd like to stay somewhere else, no sweat. See our Neighborhood Guide below for help deciding where to look.
The commercial center of the city with the tallest buildings, where all the L trains go (in a loop, get it?). There are restaurants, bars, and some shopping, but away from Michigan Ave it can be kind of dead on evenings and weekends since much of the area is office buildings. But the transit access and walkability to many tourist attractions is hard to beat.
Former meatpacking and warehouse district that has seen a ton of development in the last decade, now a destination for dining, shopping, and lofty condos and offices. There are a number of great restaurants here, though you might need to make a reservation.
Northwest from West Loop + Fulton Market are these neighborhoods. Includes some more residential and light industrial areas, but there are also great places to eat, drink, and shop on Chicago Ave. and Division St, and scattered throughout. Our venue is in the southeast-most corner of this area, in one of the more industrial stretches.
North of the Loop, east of our venue. Home to destination shopping on the Magnificent Mile, a number of bars and clubs, and walkable to the Loop and Navy Pier, it's a bustling area that's popular with tourists. Things can be overpriced but there are some solid restaurants and bars here.
Many of these are a little further from the venue and main tourist attractions but are worth visiting, or even staying in if they sound appealing to you!
Next stop north from Ukrainian Village. Fun fact: Allison and Brian met in Lauren Miller's kitchen in this neighborhood in 2016. If the weather's nice, take a walk along the 606 out to Humboldt Park. It's an elevated train line turned park, like the High Line in NYC but more relaxed.
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Further northwest along the Blue Line, this is around where we both lived when we started dating. Hip and tasty bars, restaurants, and coffee shops abound. We'd recommend The Bungalow by Middle Brow, Cellar Door Provisions, Hopewell Brewing, Bang Bang Pie & Biscuits, and Mi Tocaya Antojería. Lula is great too but they're catering ;) Check out the farmer's market on Sunday morning.
This area is near where we live now and has many great places to shop and eat. We strongly recommend Lost Larson, a Swedish-themed bakery. You can also walk east from here for Vietnamese food on Argyle St. in Uptown and one of our favorite parts of the lakefront, from Foster Beach to the dog beach and Bird Sanctuary at Montrose. It's pretty far from downtown though, plan on Ubers or longer transit journeys.
Home to University of Chicago and the Museum of Science and Industry (great for kids!) as well as the Obamas' old stomping grounds. Just know it's a little further away from downtown and the venue, and transit connection isn't great. Promontory Point is a lovely part of the lakeshore with nice city views.
A couple neighborhoods further north from River North, it's a mix of bougie housing and shopping, old Chicago institutions, and DePaul college kids (though fewer during the summer). Could be good if you want to stay near the lake but not downtown. The Lincoln Park Zoo is also free to visit and holds a special place in Allison's heart.
Southwest of downtown, Pilsen is a neighborhood known for its Latine food and culture and its art scene. It has gentrified a fair bit over the last several years but is still a lively and unique part of the city. If you're looking for good Mexican food, we recommend 5 Rabanitos and Yvolina's Tamales but there many good options.
If you live in the Northeast or on the West Coast and have a Chinatown of your own, you may not find ours that special, but if not (or if some dim sum just sounds really good), it can be a fun trip. To get there from downtown, it's connected by the Red Line L but the funnest way to get there in summer is the Water Taxi on the Chicago River.
We know that a lot of what people hear about Chicago in national media is unfortunately about crime. We think you shouldn't need to worry much during your visit. Chicago's crime stats per capita rank lower than several other US cities and the vast majority of the tens of millions of people who live and visit here don't experience it firsthand at all. Much of what you do hear about, tragic and symptomatic of decades of underinvestment, is concentrated in specific parts of the city you're unlikely to visit.
That said, it is a big city and you should use common sense, especially in crowded areas downtown. Keep an eye on your stuff, and if you end up in a place or situation that feels unsafe, leave.
We're happy to chat if you have questions or concerns!
Navy Pier? It's our Fisherman's Wharf or Times Square; almost nobody who lives here really goes there or would say it's a "must do" thing but if you really want to go we won't stop you. There are fireworks at night during the summer which could be worth going to see.
Second City? If you don't know, The Second City is a sketch and improv comedy school and theater with a storied history. It's popular for visitors and we'd give it a "yeah, that can be pretty fun"/10. Since it's partially improv and the casts rotate, you never quite know what you're gonna get. iO is another alternative with its own bonafides, or go to the Lincoln Lodge for standup.
Get out to the lake! Chicago's on Lake Michigan, one of the largest bodies of fresh water in the world. In the city, almost all of the lakefront is public land so there are lots of places to enjoy it. If you have time to get away from downtown, we like swimming here and picnicking or relaxing here and here. But you can go walk along the water and stare (or jump!) into its vastness almost anywhere. The Lakefront Trail runs along 18 miles of it, which you can walk or bike using a rental (via Divvy or a bike rental place).
Events - We only get so much summer and Chicagoans make the most of it. There are neighborhood street festivals every weekend over the summer and this weekend will be no exception. We'll update this as things get announced.
Deep dish? Sure, if you really want to. You won't need any more than a couple slices. As far as chains go, we prefer Lou Malnati's. Labriola is supposed to be good too. If you want something a little lighter, the original Chicago-style pizza is actually "tavern style" - cracker-thin crust, cut into squares.
Hot dog? Hell yeah. Here's some places you should go.
What else? Uniquely Chicago dish you probably haven't heard of - the jibarito. A Puerto Rican sandwich where the "bread" is fried plantains.
For even more inspiration, it's hard to go wrong with anywhere on the Eater 38 or Michelin Bib Gourmand lists.