Chicago, IL

Chicago got the big-city vibes you want, but friendly locals and a walkable layout make it homey and accessible all at the same time. With 77 neighborhoods to explore, your best bet is starting with the Loop or Gold Coast to hit the highlights, then fan out. Wander among the architecture that made the city famous or eat your way through town. You’ll hear a lot about deep-dish, but the tacos are also next-level, thanks to Chicago’s thriving Mexican community.

If you’re there in spring/summer, spend a do-nothing day lounging lakeside or grab a patch of grass at one of its many parks. At night, both the music and comedy scenes have put Chicago on the map. (You can’t go wrong, but Lincoln Hall and Second City are always a good time.) There’s lots more to dig into. We’ve got options below.

 

Things to see and do in Chicago, Illinois

Some things that are worth trying out:

Place to Eat:

 

Typical costs when traveling

Traveling in Chicago can cost anywhere from $400 to $900 or more per person for a weekend trip, depending on your budget and travel style. Mid-range travelers can expect to spend around $900 for a three-day trip, while those looking to travel cheaper might spend less than $390. 

 

Accommodation:
  • Hostel: $35-55 for a dorm bed.
  • Basic hotel room for two: $160-275.
  • Self-catering apartment (including Airbnb): $95-180. 
Food:
  • Fast food/counter service: $10-20 per person per meal.
  • Dinner for two: $35-70.
  • Pint of microbrew at a bar: $7-8. 
Transportation:
  • Public transport (CTA): $2.50 per ride on the L (train) or $2.25 on a bus. A 7-day CTA pass is $20. 
  • Divvy bike share: $3-5 per ride or $18/day. 
  • To and from airports: The L train is a cost-effective option, with the Blue Line (O’Hare) or Orange Line (Midway) taking 30-40 minutes and costing $2.50 to $5. 
  • Taxi/Ride-share: Can be expensive and time-consuming, especially to/from the airports. 

 

Do’s and don’ts

In Chicago, do explore the city’s diverse neighborhoods, try deep-dish pizza, and utilize the public transportation system, especially the “L” train. Don’t skip out on visiting Millennium Park and the Chicago Riverwalk, and be mindful of your belongings and personal safety, especially in crowded areas. 

 

Do’s:
  • Explore different neighborhoods: Chicago is known for its vibrant and diverse neighborhoods, each with its own unique character and attractions. Consider visiting neighborhoods like Lincoln Square, Pilsen, or the Gold Coast to experience the city’s varied atmosphere. 
  • Try Chicago-style pizza: A trip to Chicago isn’t complete without sampling a slice of their famous deep-dish pizza. 
  • Use the L train: The “L” train is an efficient and affordable way to get around the city. 
  • Visit iconic landmarks: Don’t miss Millennium Park, the Chicago Riverwalk, and other iconic attractions.
Don’ts:
  • Don’t drive downtown: Traffic can be heavy, and parking is expensive and limited, especially in the downtown area. 
  • Don’t take up the entire sidewalk: Be mindful of pedestrians and give them ample space, especially in crowded areas. 
  • Don’t be overly polite about train seats: If you see an empty seat, take it!. 
  • Don’t put ketchup on your hot dog: Chicago-style hot dogs are typically served with mustard, relish, chopped onions, a pickle spear, a tomato slice, and a sport pepper. 
  • Don’t be complacent about safety: Be aware of your surroundings, keep your valuables secure, and avoid walking alone at night in less-populated areas. 
  • Don’t skip the Navy Pier: While it’s a popular tourist spot, it can be crowded and overpriced. Consider exploring other waterfront locations for a more authentic experience. 

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