Travel & Sight-seeing

Welcome to Chicago!

Whether you’ve already decided you want to attend the most exciting, amazing, and only Umbraco conference in the United States, or whether you still need some convincing, we’ve put together a travel guide with all of the most amazing destinations and tips to make your trip more enjoyable.


From O’Hare Airport

Flying into O’Hare airport is the easiest from a public transportation standpoint. The train line goes to and from the airport and loops around many stops in downtown Chicago.

There are signs all over the airport directing you to the train station underground. You will get on the Blue Line (the only train that goes to/from the airport, so no need to figure out which train to get on).

When you get closer there will be blue kiosks that allow you to purchase a train ticket. You can either purchase a day pass (if you plan on using the train a lot in one day) or a single ride ticket to get you from the airport to your destination.


If You’re Staying at The Robey Chicago

If you are lucky enough to get one of the rooms in our room block at The Robey Chicago, it’s only about a 35 minute train ride directly to your hotel.

It’s located in a section of Chicago called “The Six Corners” and is one of the hippest areas in the city. There is a ton of cool places for food and for shopping, and it’s only two stops away from the venue.

When you get off the plane, follow signs to get on the Blue Line and take it all the way to the Damen Blue Line stop. Once you get off the train, you’ll head north immediately and see the tallest building in the neighborhood. That’s The Robey.

Drinking and Eating at the Robey:

  • They have a bar on the rooftop that offers amazing, unique views of the city. It’s called the Up and Up and it’s swanky. Expect drinks prices to be higher, but it’s worth one if you’ve never been. Also get there early if you don’t want to wait.
  • They have another bar on the 6th floor called the Cabana Club that is worth a visit as well. Has a big pool with tables around an open air balcony.
  • They have a lounge/bar on the 2nd floor that is great for getting work done in the morning, grabbing a quick coffee/pastry, or getting a beer.
  • They have a restaurant on the bottom floor that has good brunch and lunch food. There are other great food options in the area, but in a pinch the restaurant is very solid.

If You’re Staying Elsewhere

There are many hotels downtown that offer great rates for travelers. If you are looking to be budget conscious, our recommendation would be to look for hotels along the Blue Line train. This is a great way to get around the city and the venue is right off the Chicago Blue Line stop. A few stops will take you no longer than 20 mins to get to the venue, so you are pretty safe anywhere along the train line.

If you don’t mind spending a bit more to get the hotel you really want, downtown to the venue via cab or rideshare will take you no more than 10-15 minutes depending on traffic.

Check out our full guide to Hotels & Lodging.

Stuff To Do

You definitely won’t be able to get to all of it just one week or weekend, but depending on what you like to do, Chicago has a ton of places to visit for any type of traveler. If you’re heading here early or staying for the weekend, here’s a list of some awesome places to visit.


Chicago’s culinary scene has completely blown up and continues to grow. There are more amazing places to eat at then we can count, but here are some of our favorite neighborhood joints:

  • Green Street Smoked Meats (Fulton Market). Awesome warehouse that offers meats that are smoked each day. Get there as early as possible because once the meat’s gone, it’s gone!
  • Kuma’s Corner (Fulton Market). Some of the craziest burgers you’ll ever eat. The only thing louder than the menu is the heavy metal they play to amp the vibe.
  • Piece Pizza (Wicker Park). Brewery and pizzeria, this crowded neighborhood staple dishes out giant pizzas and homemade brews. If you want extra special, try out the Hot Doug’s Atomic pizza which blends a long lost, recently closed Chicago sausage shop with an already amazing pie.
  • Jeni's Ice Cream (Wicker Park). A neighborhood staple, this great icream shop is Jeni's second shop in Chicago just down the street from The Robey. Have a seat and enjoy a scoop and some hometown Intelligentsia Coffee. Or, get a cone or pint to go and stroll the historic neighborhood.


Bars are a dime a dozen in Chicago, but if you’re looking for something truly unique, check out these favorites:

  • The Violet Hour (Wicker Park). Funky, swanky drink joint with no windows and no standing room. The mural out front changes monthly and you’d be hard-pressed to find the door if you weren’t looking for it. Another place to get to early if you want a chance at getting in. Not for the casual get together, more for the experience.
  • Emporium (Wicker Park). Part bar, part arcade, Emporium offers patrons the chance to go back in time to play some of their favorite arcade games. From NBA Jam to The Simpsons to Space Invaders, this bar has something for everyone.
  • Hopleaf (Andersonville). This bar is pretty far north, but anyone who’s anyone that knows beer in Chicago knows that this is a must visit bar. They have a ton of beers in-house from all over the world and have amazing Belgium fare that’s hard to resist.


  • Goose Island Brewery. Located in the industrious Fulton Market neighborhood, this relatively new tap room is small but mighty. They generally have some tap room exclusive beers that you won’t be able to get anywhere else, and have super cool merchandise you can take back as a souvenir. Get a tour and you’ll go home with a tap room exclusive glass a few pints in your stomach.
  • Great Central Brewing. Located a couple of blocks away from Goose Island, this brewery actually has a knack for brewing other brewers beer. They offer up their space to brew more for other breweries in the area and, lucky for us, also have them on tap. Pair it with Goose Island for an awesome night of trying many different beers.
  • Half Acre Brewery. A Chicago staple, Half Acre’s Daisy Cutter is a beer that continues to make a name for itself. But don’t be fooled, Half Acre has a TON of amazing beers that would satisfy any type of beer lover. It’s a little further north than the other breweries on the list, but worth the trip if you love your beer.
  • Lagunitas Brewery. Originally from California, this brewery decided to take up shop in the Pilsen neighborhood of Chicago and build out a tap room for the locals. Truly a unique experience, this tap room overlooks the whole brewing operation in the center of the facility, serving both bar fare and delicious beer flights along the way. Don’t be surprised if they have a live musical act on stage to sweeten the deal.
  • Ballast Point Brewery. One of the newest breweries to grace Chicago, this San Diego local brewery just set up shop in a brand new tap room in Fulton Market. If you choose one of the Fulton Market options on the food list, it would be a good idea to pair it with a beer from Ballast Point. They also have pretty tremendous food as well if you want to belly up and bunker down.

Touristy Stuff

  • Navy Pier. This is the pier that everyone talks about with the Ferris Wheel. If you must see it, I recommend avoiding the restaurants. They are touristy and not worth the money spent. If you are into drinking, keep walking down the pier until you hit the beer garden at the end. It’s like hitting the pot of gold at the end of the touristy rainbow.
  • Michigan Avenue. Our famous strip for shopping. If you’re into that kind of thing, it’s worth a once over if to just duck in and out of shops. The number of shops on the strip are almost overwhelming. Be prepared to dodge a lot of people on the sidewalk, but still an experience.
  • Museum of Science and Industry. Probably our coolest museum, they always have neat exhibits going on. It’s touristy, but of all the things to go to, this would be one to add to your list.
  • White Sox/Cubs Game. Depending on your allegiance (and to be clear, Chicagoans have severe allegiances), check out a baseball game. Both stadiums are awesome and offer different experiences, so you’d be a winner either way.
  • Architecture Boat Tour. Chicago has some amazing architecture and it’s hard to see if you’re walking downtown. You also miss out on the history. Lucky for you, Chicago is well known for its architecture boat tours that mosey along the Chicago River pointing out all of the famous historic and modern buildings. (If your not into architecture or boats, there are other tours you can try.)
  • Second City. If you’re familiar with Saturday Night Live, you’re familiar with some of the comedians that had their start at this famous improv stage. Catch a show any night of the week to see what could be the future stars of the improv world.
  • Millennium Park. Green space, public art (this is where you'll find that mirrored-bean), and events. A great place to check out if the weather is nice.