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What is a must see/do in 4 Nights in Chicago for two 30 something women

We will arrive in Chicago May 27 and leave May 31st

We love walking so we want to stay in a neighborhood with lots of activity, we are using airbnb for most of our trip but are still unclear where best to stay in this City.

We also would like some  "Must See/Do" recommendations. We love food, drinks, art and live Music.


7 Answers

top answer by
ross from Chicago


So many great neighborhoods: River North, Loop, Bucktown/Wicker Park, Wrigleyville, The West Loop.

Lots of action in all of these places. If you want to stay in a cool area and walk to a lot of fun things ( restaurants , shopping, museums ) head to the River North area downtown. River North has lots of galleries.

West Loop/Randolph Street has great restaurants and galleries. Bucktown / Wicker Park has funky cool shopping.

Mentioned in this answer:

  1. River North (neighborhood)
  2. Loop (attraction)
  3. Bucktown (neighborhood)
  4. Wicker Park (neighborhood)
  5. Wrigleyville (neighborhood)
  6. West Loop (neighborhood)
7 thankscomments (1)

answered by
Maggie from Chicago

The Art Institute of Chicago is a must. restaurant inside has amazing food too. Chicago Architecture Foundation River Cruise starting on Chicago River. Chicago Detours Walking Tour of city.

6 thankscomments (1)

answered first by
Courtney from Los Angeles

I would definitely check out the Second City comedy troupe. I saw them last time I was there and it was great. The Wicker Park area is a big favorite of mine--tons of little bars and music venues as well as some great shopping. 

Mentioned in this answer:

  1. Second City (attraction)
  2. Wicker Park (neighborhood)
6 thanks

answered by
Jason from Singapore

The Original Garrett Popcorn Shops. The very first McDonald's: McDonald's Store #1 Museum. Must visit Millenium ParkAl's Beef, and the many many world's famous steak houses in Chicago. Don't forget too that Chicago is THE birthplace of improv theatre. So you'll have a great laugh doing that as well. Sorry it's so food heavy :)

Mentioned in this answer:

  1. Garrett Popcorn Shops (restaurant)
  2. McDonald's Store #1 Museum (attraction)
  3. Millenium Park (attraction)
  4. Al's Beef (restaurant)
5 thanks

answered by
Sarah from Houston

Chicago is an amazing city especially to walk around and to see all the beautiful sights. The question is what do you want to experience in the city in that time? I would say Second City for improv, i.o. is also great for improv and the Green Mill Jazz Club is a very cool speakeasy from like the 1920s.

For food you have a wide assortment to choose from, I love to suggest Geja's Cafe for a very romantic setting it is a fondue restaurant. For just great food and a great Chicago feel there is RJ Grunts which there claim to fame is the 'first' salad bar and they have great burgers. RJ is located within walking distance of the zoo.

I think that The Field Museum is great and the Shedd Aquarium are must-sees if you love to walk around museums as well as the art institute. Millennium Park is also nice to walk through and I'd say to come back to visit just so you can see even more! 

Mentioned in this answer:

  1. Second City (attraction)
  2. Green Mill Jazz Club (attraction)
  3. Geja's Cafe (restaurant)
  4. RJ Grunts (restaurant)
  5. The Field Museum (attraction)
  6. Shedd Aquarium (attraction)
  7. Millennium Park (attraction)
4 thanks

answered by
D from Orland Park

If you love shopping, Michigan Avenue can't be beat. Start at the 900 building and walk to the river. So many good restaurants and stores. If you like the night scene, Rush Street is also very popular. If it's a nice day, check out Navy Pier and take a Shoreline cruise. Great views if the city!

Mentioned in this answer:

  1. Michigan Avenue (attraction)
  2. Rush Street (attraction)
  3. Navy Pier (attraction)
4 thanks

answered by
Jinny from Los Angeles

 Hi Victoria, 

If you like walking, then you'll like my Top 10 Low-Budget Things to do in Chicago from my blog. In brief summary:

1. Eat pizza. At any restaurant or hole in the wall, whether it's deep dish or thin crust, it tastes like the ones you'd find in Italy.

2. Get up to the Willis Tower

3. Walk around Millennium Park. You'll have yourself an album full of great photos from this place. 

4. Buckingham Fountain

5. Rent a city bike. My friend and I found so many off the beaten road artsy places by just biking around the city.

6. Go to the many spectacular museums.

7. Take an architectural boat ride. A little pricey if you're not into architecture, but it has really great views of the city.

8. Chicago Riverwalk

9. Get some Garrett Popcorn Shops. Best popcorn I've ever had. There's always a line, but goes by fast. 

10. Dinner at the Navy Pier

Mentioned in this answer:

  1. Willis Tower (attraction)
  2. Millennium Park (attraction)
  3. Buckingham Fountain (restaurant)
  4. Chicago Riverwalk (attraction)
  5. Garrett Popcorn Shops (restaurant)
  6. Navy Pier (attraction)
1 thanks

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