Stay – Similar prices with the rest of America. A night in a hostel costs you around 20$ (€18). For a single (two person) room you’ll pay triple, around $60. (€55)
The closer to the center, the more expensive it usually gets. For the same room in the city center, add another $40. So about $100. (€90)
You can see all accommodations + prices here.
Eat – There’s plenty of eating possibilities in Chicago. The high competition between great restaurants keep the prices quite low. Prices for lunch or dinner are between $9 and $30 a person. A delicious, mouthwatering deep dish pizza costs $15 (€14) a person. If you share your pizza, it’ll be cheaper. Only $20 to $25.
Transport – The public transportation in Chicago is excellent. From the airport you can take the metro to the city center. It’s quite a drive, but it’s very cheap in comparison to other possibilities.
For the cost, it all depends on where you need to be. Most of the times it’s betwee $5 or $2,25. If you plan on taking public transportation multiple times during your stay, a week pass is probably a good idea.
Free zoo! – Go to Lincoln Park zoo and look at the animals. There is no entrance fee and the views from there are amazing. You can see the skyline of Chicago from a little bridge in the middle of the park.
Skydeck during day and night – If you plan on going to the Willis Tower (and the skydeck) try to go in the early evening. If you go a little before sundown, you can see the city in normal daylight, sundown AND night. Three views you have to see while you’re there!
Keep in mind that you need some extra time for waiting in lines.
Willis Skydeck – I already spent a lot of time gazing at cities from top decks in skyscrapers because every time the views are just amazing. However, my absolute favourite view was from the WIllis Skydeck. Probably just because there are glass booths where you can stand in. It seems like you’re floating above the city, because you’re just standing on a glass floor. No pussies allowed!
Chicago Millenium Park – A cosy park in the center of Chicago, where you can also see the Cloud gate (the locals sometimes call it ‘The Bean’). Try to go to one of the many open air concerts in the middle of the park. If you’re lucky enough, you can even go to a free concert.
Magnificent Mile – Shopaholics: watch out! The magnificent mile starts at the Chicago river until Oak Street and is part of the famous Michigan Avenue. Be prepared to spend a lot of dollars, because the appealing outlet stores are too tempting to avoid!
Spotting architecture – Chicago is known for its great architecture. By doing a boat tour on the Chicago river, you get a unique vantage point on all these beautiful buildings next to the river banks. You’ll get informative comments from well educated guides.
Art Institute of Chicago – I never really like museums, and for the Art Institute of Chicago I made no change of heart. However, I put this museum in this list because it is supposed to be one of the nicest museums in the world. There is a big collection of famous art work from famous painters and other artists. Next to these big pieces of art, you can also find smaller exhibitions. I don’t recommend this museum to people who are just not very fond of museums. But then again… Art is something very subjective… So maybe you do like it?
Look at the skyline – Let your jaw drop open at the sight of the Chicago skyline. The best places to look at Chicago’s horizon are (in my opinion) in Lincoln Park Zoo (on the bridge, near the swamp), the Adler Planetarium and the Navy Pier.
Navy Pier – Nice for you and the kids. This permanent fair has a ferris wheel and a quite nice vantage point over the Michigan Lake and the city.
Deep dish pizza – The culinary specialty of Chicago is a deep dish pizza. The pizza is a couple of centimeters / inches high and within this delicious crusts are several layers of mozzarella, tomato sauce and whatever you want to add.
The best places to eat this delicacy are Giordano’s and Lou Malnati’s. Can’t eat the full pizza? Ask your waiter to take it home. Way too good to just throw away!
Busses during rush hour – Walking is a lot faster. If you see that the traffic doesn’t move, just get off. Otherwise you’ll lose some valuable sightseeing hours. Try to get into a metro station if there is one nearby.
Winter – You can’t really prepare yourself on cold winter days in Chicago if your not from there. The thermometer drops significantly and the heavy snow will definitely leave you inside your hotel for a couple of days. Try to go during summer for a better experience.
Dangerous neighbourhoods – Don’t go too far out of the city center. Leave neighbourhoods like Austin, West-Englewood, Humboldt Park and South Shore alone. There are some other places you should ignore, but if you stay close to the center you’re far away from these.