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In Chicago in early May for one night only; suggestions?

My husband has never been to Chicago. What are the best places to show him just how great the city is?

10 Answers

top answer by
Tyler from Newport Beach, California

Be sure to go to Cubs game if you are a sports fan, The Bean is amazing and Lou Malnatis Pizzeria is the best pizza.  The architecture boat tour is also really cool. 

Mentioned in this answer:

  1. The Bean (attraction)
3 thankscomments (1)

answered by
Sinead from Chicago

I would recommend staying somewhere cool, like the Hotel Lincoln. From there you can walk to see a show at Second City (never disappoints!) and then head a little farther south and check out a few key roof-top bars (Drumbar, ROOF on theWit, Nomi Restaurantat the Park Hyatt, etc.). Have fun!

Mentioned in this answer:

  1. Hotel Lincoln (hotel)
  2. Second City (attraction)
  3. Drumbar (attraction)
  4. ROOF on theWit (attraction)
  5. Nomi Restaurant (restaurant)
1 thanks

answered by
Albert from Santa Monica

I went on Memorial Weekend a few years back and checked out a Cubs game.  It's great even if you're a casual baseball fan.  Personal highlights for me were the river architectural tour, Willis Tower, great dining, and checking out a night club where DJ Trentino was DJing.  You also can't go wrong with Millenium Park, Magnificent Mile shopping, and local deep dish pizza joints like Giordano's and Lou Malnati's Pizzeria.  If you're into running and/or biking the area near Lake Michigan is a must see as well.  Happy travels!

Mentioned in this answer:

  1. Willis Tower (attraction)
  2. Millenium Park (attraction)
  3. Magnificent Mile (attraction)
  4. Giordano's (restaurant)
  5. Lou Malnati's Pizzeria (restaurant)
  6. Lake Michigan (attraction)
1 thanks

answered by
Emily from Chicago

Hi Rebecca-

This is a tough question! Without knowing what your husband is into nor where you guys will be staying, I'd suggest checking out a few places downtown and then heading into a couple different neighborhoods for dinner and drinks. I might start downtown at Millennium Park to see the fountains, The Bean (the bean) and do plenty of people watching! Then either jump on the blue line and head northwest to Wicker Park/Bucktown/Logan Square or jump on the brown line headed north and check out Old Town/Lincoln Park. The weather should be nice in May so make sure to leave yourselves some time to walk around and enjoy the neighborhoods, it's one of Chicago's best features!

Mentioned in this answer:

  1. Millennium Park (attraction)
  2. Wicker Park (neighborhood)
  3. Bucktown (neighborhood)
  4. Logan Square (attraction)
  5. Old Town (attraction)
  6. Lincoln Park (attraction)
  7. The Bean (attraction)
1 thanks

answered by
Lindsay from Denver

I second/third/fourth the architectural river tour. Make sure to do the river tour not the lake version. It's just more interesting. I'm from Chicago and my mom continues to take every visitor on this tour every time because it's such a great introduction to Chicago.  

Btw, Chicago deep dish is certainly one of a kind, but most Chicagoans are over it. I will put in a plug for Gino's East though, my favorite over Lou Malnati's Pizzeria and Giordano's.

Also, definitely get to the lakefront. Rent bikes or just walk/run along Lake shore Drive.  

Lastly, be prepared that May weather isn't always spring-like. It's a total crapshoot so check before you pack!

Mentioned in this answer:

  1. Gino's East (restaurant)
  2. Lou Malnati's Pizzeria (restaurant)
  3. Giordano's (restaurant)
1 thanks

answered by
Dabs from Chicago

If you get nice weather, nothing beats being on the Lakefront.  Either renting bikes and going for a ride or taking one of the River or Lake cruises.  For architecture go on the Chicago Architecture Foundation river cruise, if you just want a boat ride, Shoreline or Wendella is fine.  Just remember that it's cooler by the lake and dress warmly.

Eating is an important part of any visit to Chicago, I'd try one of Chicago's famous pizza places, either Giordano's for stuffed pizza or Lou Malnati's Pizzeria for deep dish.  There are multiple locations of both so you should be able to find one close to where you are going.

For great views, I take people to the The Signature Lounge at the Hancock, no charge except for the rather pricey drink if you want to sit down.

If the weather is frightful, there are great museums depending on his interests-art, history, fish, natural history, contemporary art, astronomy.

Mentioned in this answer:

  1. Chicago Architecture Foundation (attraction)
  2. Giordano's (restaurant)
  3. Lou Malnati's Pizzeria (restaurant)
  4. The Signature Lounge (attraction)
1 thanks

answered by
Melissa from Chicago

If I had only one day to spend here, I would do the following: start at Lincoln Park Zoo early before the crowds and afterwards walk through Lincoln Park (and the nature boardwalk) to the Lakefront Trail. Walk the lakefront or rent a Divvy Bike to head south. Park the bikes to wander around Millennium Park (take some selfies in the bean!) and visit one of the best museums in the world, The Art Institute of Chicago. Have a drink at The Signature Lounge at the John Hancock Building for the view before dinner. For fancy food, I would say Perennial Virant, for deep dish pizza Giordano's, and for Italian beef or hot dogs Portillo's. Have fun!! 

Mentioned in this answer:

  1. Lincoln Park Zoo (attraction)
  2. Lakefront Trail (attraction)
  3. Millennium Park (attraction)
  4. The Art Institute of Chicago (attraction)
  5. The Signature Lounge (attraction)
  6. Perennial Virant (restaurant)
  7. Giordano's (restaurant)
  8. Portillo's (restaurant)
1 thanks

answered by
Christa from Bolingbrook, Illinois

I second the Cubs game. I HATE baseball and I still had so much fun. The game is okay, after the game is where the fun is at :) Check out the Cubby Bear after the game and from there just follow the masses. As far as Pizza goes Lou Malnati's Pizzeria is my favorite and Pizzeria UNOis good too. Chew slooowly bc the cheese is thick!! lol. Wicker Park is my favorite neighborhood to go out in. It's a very hipster neighborhood. My favorite places to go there are Piece Pizzeria and Brewery (get a white pizza and marinara sauce to dip it in), and Emporium Arcade Bar Literally an Arcade in a bar. Sooooo much fun. You can do brunch at Bongo Room. I like the Shedd Aquarium and The Bean is Okaaaay but not a huge deal to me. (Mind you I am from the Chicago area so maybe the awe has worn off.) If you like to dance I think that Hub 51 downtown is fun. Hub 51 on the top floor is a bar and in the basement SUB 51 is the club. For the late night munchies get a Polish Sausage Maxwell Street Grill...sooooooo goooooood!!!! If you wanna go shopping go to Magnificent Mile (AKA Michigan avenue) and Water Tower Place. Enjoy our city :) P.S. my friend visited from NY and he got such a cute little apartment for the weekend from airbnb. I would definitely check that out!

Mentioned in this answer:

  1. Lou Malnati's Pizzeria (restaurant)
  2. Pizzeria UNO (restaurant)
  3. Wicker Park (neighborhood)
  4. Piece Pizzeria and Brewery (restaurant)
  5. Emporium Arcade Bar (attraction)
  6. Bongo Room (restaurant)
  7. Shedd Aquarium (attraction)
  8. Hub 51 (restaurant)
  9. SUB 51 (attraction)
  10. Maxwell Street Grill (restaurant)
  11. Magnificent Mile (attraction)
  12. Water Tower Place (attraction)
  13. The Bean (attraction)
1 thanks

answered by
Jose S from Antioch

My typical Chicago tour for visitors:

1. Navy Pier (Can take Architecture Boat Tour from there)

2. Millennium Park ("The Bean")

3. N Michigan Ave

4. Wrigleyville (Bonus if there is a game)

Mentioned in this answer:

  1. Navy Pier (attraction)
  2. Millennium Park (attraction)
  3. N Michigan Ave (attraction)
  4. Wrigleyville (neighborhood)
1 thanks

answered by
Brady from Manhattan Beach

Have dinner at Girl & the Goat. You will have drinks at Violet Hour. Stay at the Waldorf Astoria Chicago.

Mentioned in this answer:

  1. Girl & the Goat (restaurant)
  2. Violet Hour (restaurant)
  3. Waldorf Astoria Chicago (hotel)

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