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How many days should I spend in Chicago?

I'm moving to Toronto, Canada but want to do a little bit of traveling before hand. I can always go back if I like, but suggestions of a good amount of time to cover an experience in Chicago?? 

8 Answers

answered by
Madison from Chicago

If you can spend an entire week in Chicago I would highly recommend it. There is a vast difference in the neighborhoods here as well as the attractions. I'd recommend checking out some of the museums. The Art Institute of Chicago is particularly wonderful, especially the newer modern wing which has a great spot for lunch Terzo Piano. The Shedd Aquarium and Museum of Science and Industry are also great.

I would 100% disagree about the lack of amazing food in Chicago, there are a myriad of world class options, you just have to be willing to leave downtown and explore some of the neighborhoods Chicago has to offer. For example, head to Logan Square via the Blue Line and try out Longman & Eagle for dinner and Lula Café for brunch. While in Logan, check out The Whistler or Billy Sunday for cocktails. I would also highly recommend checking out some of the restaurants in the west loop like Sepia and Girl & the Goat. Some other notable neighborhoods include Lincoln Square Neighborhood Wicker Park and Pilsen for a variety of cultural and culinary experiences. Enjoy!

Mentioned in this answer:

  1. The Art Institute of Chicago (attraction)
  2. Terzo Piano (restaurant)
  3. Shedd Aquarium (attraction)
  4. Museum of Science and Industry (attraction)
  5. Logan Square (attraction)
  6. Longman & Eagle (restaurant)
  7. Lula Café (restaurant)
  8. The Whistler (restaurant)
  9. Billy Sunday (attraction)
  10. Sepia (restaurant)
  11. Girl & the Goat (restaurant)
  12. Lincoln Square Neighborhood (attraction)
  13. Wicker Park (neighborhood)
  14. Pilsen (attraction)
1 thankscomments (1)

answered by
Dabs from Chicago

Depends on what you like to do and when you are coming.  If it's in the summer months, I'd suggest anywhere from 3-7 days depending on what you can spare.  Chicago has great museums-art, history, science, natural history.  It has the free Lincoln Park Zoo inside the city and the Brookfield Zoo in the suburbs.  There's the beautiful Chicago Botanic Garden north of the city.

In the warmer months there are a ton of festivals, usually with music and food.  Bike riding along the lakefront is a fun thing to do and I'd highly recommend a boat ride either on the River or the Lake or both.

There are interesting neighborhoods to visit, there are two rather tall buildings with great views, there's fabulous theater including the Goodman Theatre, Steppenwolf Theatre, Chicago Shakespeare Theater, Second City and whatever Broadway style show happens to be in town.

I'd absolutely disagree that Chicago dining is overrated, there are some of the top ranked restaurants in the country like Alinea, there are regional favorites such as deep dish pizza, steakhouses and Chicago style hot dogs, there are just about any kind of ethnic food you'd want and there are a ton of mid tiered restaurants that get plenty of critical acclaim from both inside the city and outside.

Mentioned in this answer:

  1. Lincoln Park Zoo (attraction)
  2. Brookfield Zoo (attraction)
  3. Chicago Botanic Garden (attraction)
  4. Goodman Theatre (attraction)
  5. Steppenwolf Theatre (attraction)
  6. Chicago Shakespeare Theater (attraction)
  7. Second City (attraction)
  8. Alinea (restaurant)
1 thanks

answered by
Jillian from Los Angeles

Hi Kiarna! 

I've most recently lived in Chicago for the past 8 years before moving to LA, so here's what I'd say: take at least 3 days, maybe 4.

For your first trip, this should give you a decent time to explore the many, amazing neighborhoods Chicago has to offer without over-doing it for your first time. A few can't miss neighborhoods (and food recs to go along!): 

Have fun and let me know if you need anything else!

Mentioned in this answer:

  1. River North (neighborhood)
  2. Lou Malnati's Pizzeria (restaurant)
  3. N Michigan Ave (attraction)
  4. Hancock Building (attraction)
  5. Bavette's Bar and Boeuf (restaurant)
  6. GT Fish & Oyster (restaurant)
  7. Momotaro (restaurant)
  8. West Town (neighborhood)
  9. Au Cheval (restaurant)
  10. Bucktown (neighborhood)
  11. Big Star (restaurant)
  12. Damen & Division (attraction)
  13. Logan Square (attraction)
  14. Longman & Eagle (restaurant)
comments (1)

answered first by
Justin from Phoenix

You might want to check out this Trippy thread. It has some useful bits about Chicago. If you want to see a really great city in the United States, I'd direct you to Portland or Seattle. They have a lot of character and quirkiness. I like the food in Portland 10 times better than Chicago food, too. I've never seen a city overrate its restaurants more than Chicago. 

Mentioned in this answer:

  1. Portland (city)
  2. Seattle (city)
1 thanks

answered by
Cheryl from Wisconsin

A long weekend is plenty to hit the main tourist attractions. If there is a good show to see, you might want more time. Check out Second City comedy and the The Chicago Theatre, plus the main museums like Shedd Aquarium, The Art Institute of Chicago and Field Museum of Natural History.

Mentioned in this answer:

  1. Second City (attraction)
  2. The Chicago Theatre (attraction)
  3. Shedd Aquarium (attraction)
  4. The Art Institute of Chicago (attraction)
  5. Field Museum of Natural History (attraction)

answered by
Tonco from London

I went to Chicago in November and 2 days were enough

answered by
Tim from Chicago

I started with a long weekend, and it turned into 30 years!

As they say, Kiarna, it depends. If you are into museums and the like, there are some world class things to see and that will take some time. The Art Institute of Chicago, Museum of Science and Industry, Field Museum of Natural History, Shedd Aquarium, etc. Of them, only the Art Institute is really "in the heart" of the city. I'd say it's a don't miss. Millennium Park is across the street.

If you like to shop there are lots of the usual places, and if you head up and out into some of the neighborhoods there are more unique and special retail locations. I'd spend some time in Lincoln Park, at the Lincoln Park Zoo and Conservatory.

If you are here in decent weather, there is nothing like the experience of a Cubs game, and maybe trying to spend some time out on the lake. A walk, run or bike ride along the lake is an awesome way to spend a morning.

Long answer, but I'd suggest coming after April, and I'd stay three nites. You can get a lot done in that time.

Mentioned in this answer:

  1. The Art Institute of Chicago (attraction)
  2. Museum of Science and Industry (attraction)
  3. Field Museum of Natural History (attraction)
  4. Shedd Aquarium (attraction)
  5. Millennium Park (attraction)
  6. Lincoln Park (attraction)
  7. Lincoln Park Zoo (attraction)
  8. Conservatory (attraction)

answered by
Tanya from Ottawa

I live in Ottawa, ON which offers direct flights to Chicago and in the past 5 years, we've been three times between May and Labour day weekend at the beginning of September. Each time we visit it's for three days and always feel content after each visit...anything we miss, gives us an excuse to visit again.

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