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Things to do during a long weekend in Chicago for anniversary

I'm taking my lady to to Chicago in June to celebrate our anniversary. I haven’t been there since college so I just remember bits and pieces of it and would love some help putting together a plan. We’re taking a long weekend for four days and I’m trying to figure out a basic itinerary. I’d like any advice about how best to see these attractions and/or what other attractions we should see or what we should skip. Some nice dinner recommendations would be awesome too. Here's what I'm thinking:

  • Art Institute of Chicago
  • Millennium Park
  • Field Museum
  • The view from Sears Tower
  • The Zoo
  • The Tiffany ceiling at the Cultural Center and Tiffany ceiling at Marshall Fields
  • Maybe a ball game at Wrigley Field?
  • Chinatown
  • Magnificent Mile
  • Polish Village
  • Some kind of walking/biking day by the water
  • Maybe Greektown—we’ve heard about this but we’re not sure what it is
  • Hyde Park
  • Would like some suggestions about what to see in “The Loop”

ETA just in case in helps anyone: I haven't decided on a budget, but I'd like to do activities and experience meals that are reasonably priced and if there's something that's worth it, I also wouldn't mind splurging.

10 Answers

top answer by
Jillian from Los Angeles

You can't beat Chicago in June. I grew up in the north suburbs and have lived in Chicago the past 8 years, so hopefully I can help!

Out of all the places on your list, I'm most familiar with the near north side. 

Personally, I would skip the zoo and the Field Museum. However, I would check out the The Art Institute of Chicago. Their exhibitions are beautiful if you enjoy art. It's located in the loop, so this would also give you a chance to walk around the area. Close by is  Millennium Park which is fairly touristy, although do check out the giant bean if you haven't seen it. They also have a concert series in the summer that might be of interest to you.

From there, I'd head north and walk over the river for a glass of wine and charcuterie at The Purple Pig. Take in the views of the river on your way there. 

The Sears Tower is now actually called the  Willis Tower. I would also add this to the list for the views 103 floors up. If you're feeling brave, you can walk out on the glass ledge to experience the view straight down too! However, it's really touristy, so keep that in mind. Another spot to check out the views at night is the  The Signature Room at the 95th. I would go here for an after dinner drink, and request a table looking out over the city lights. 

I saw you mentioned Marshall Fields, which is now  Macy's on State Street. I honestly don't know much about the Tiffany ceiling so can't be of help there. 

Definitely head to  Wrigley Field for a Cubs game!  Wrigleyville is a really fun area, but on game days (win or lose!), the streets are often filled with tipsy 20-somethings. All in all, if you haven't been to a Cubs game and enjoy live baseball, it's one of the best stadiums and areas to take it in. 

For walking along the water, head to  North Avenue Beach where there's a path that takes you as far as you'd like by the lake. It gets pretty crowded in the summer, but nonetheless it's beautiful.

One of my absolute favorite restaurants for a special occasion is Next. They switch the menu about every three months with a different cuisine/theme, and the presentation and service is pretty flawless. It's really a must-do all around. You do need to purchase tickets in advance and can find ticket information here: It can be hard to get tickets, so be sure to check their Facebook page for additional updates as well.

Hope you have an amazing anniversary and enjoy all the city has to offer!

Mentioned in this answer:

  1. The Art Institute of Chicago (attraction)
  2. Millennium Park (attraction)
  3. The Purple Pig (restaurant)
  4. Willis Tower (attraction)
  5. The Signature Room at the 95th (restaurant)
  6. Macy's (attraction)
  7. Wrigley Field (attraction)
  8. Wrigleyville (neighborhood)
  9. North Avenue Beach (attraction)
  10. Next (restaurant)
6 thankscomments (1)

answered first by
Tim from Chicago

Hey Will,

Good choice on coming to Chicago! I've lived here most of my life and have a few suggestions...

Sounds like you're going to a lot of the tourist spots so I'll focus on restaurants since that's my specialty.

Greektown is cool, I live in that area--but it's mostly just a few restaurants and you'd be much better off checking out most of the restaurants around Randolph street.

Girl & the Goat is awesome, a bit pricey. Stephanie Izard is the chef and one of the few female winners of the show Top Chef. Hands down my favorite dining experience in Chicago.

Little Goat is Stephanie Izard's other spot across the street which is a bit more affordable and is more of a diner feel. AWESOME food there as well.

Nellcôte is another great spot just down the street. Haymarket Pub & Brewery is also on that same Randolph/Halsted intersection and is a great craft beer place. (They also brew their own beer there) Good spot to get a beer or two anytime.

Highly recommend going to a rooftop bar while you're here if the weather is nice. There are a bunch of them: Drumbar, Epic, Citizen Bar Chicago, and theWit all have great rooftop places. Citizen's is the most laid back, and the others are a bit more upscale.

For shopping, don't be scared to head over to Wicker Park. Lots of fun places in that area around Damen/Milwaukee/North avenue intersection.

Mentioned in this answer:

  1. Greektown (attraction)
  2. Girl & the Goat (restaurant)
  3. Little Goat (restaurant)
  4. Nellcôte (restaurant)
  5. Haymarket Pub & Brewery (attraction)
  6. Drumbar (attraction)
  7. Epic (restaurant)
  8. Citizen Bar Chicago (attraction)
  9. theWit (hotel)
  10. Wicker Park (neighborhood)
5 thankscomments (2)

answered by
Ted from Chicago

You definitely want to add a tour of the Chicago River through either Wendella Boats or Chicago Architecture Foundation River Cruise I live in Chicago and this is one of the things I do not get sick of when family friends are in town.  I also recommend visiting Chicago neighborhoods. You have some good ones with Wrigleyville, Hyde Park, Polish Village, and Greektown. A couple of other good ones are Andersonville (there is the The Green Mill jazz club here), Wicker Park, Uptown, and Lincoln Square Neighborhood. You have a good list started. Have a great time.

Mentioned in this answer:

  1. Wendella Boats (attraction)
  2. Chicago Architecture Foundation River Cruise (attraction)
  3. Wrigleyville (neighborhood)
  4. Hyde Park (neighborhood)
  5. Polish Village (neighborhood)
  6. Greektown (attraction)
  7. The Green Mill (attraction)
  8. Wicker Park (neighborhood)
  9. Uptown (neighborhood)
  10. Lincoln Square Neighborhood (attraction)
4 thankscomments (1)

answered by
Caroline from New York City

Second on the Girl & the Goat! Also, I've never been there, but if you can swing it, I'd do an anniversary dinner at Alinea. It was voted the 6th best restaurant in the world by Restaurant Magazine--also has three Michelin big deal. The menu is set that day, very unique, and very pricey but worth it. The reservation process is kind of tricky--I'd check out their website for more info--but it would be a very memorable anniversary dinner.

Mentioned in this answer:

  1. Girl & the Goat (restaurant)
  2. Alinea (restaurant)
4 thankscomments (1)

answered by
Lori from Brooklyn (New York)

Especially in June, don't miss the Chicago Architecture Foundation River Cruise, you get the history of Chicago, the history of the architecture and a nice boat ride!

Mentioned in this answer:

  1. Chicago Architecture Foundation River Cruise (attraction)
3 thankscomments (1)

answered by
Dominique from Chicago

You can take her anywhere in Chicago. It's nice down there mostly downtown.

Mentioned in this answer:

  1. Chicago (city)
1 thanks

answered by
Savion from Muncie

       You might not mind going to Willis Tower and enjoying the view or also look at some magnificent artwork while there it is a very fun city.

Mentioned in this answer:

  1. Willis Tower (attraction)
2 thankscomments (1)

answered by
Dan from Memphis

Based on suggestions and your list, you should consider purchasing a CityPASS. I wish I had during my last visit with the kids. We hit the aquarium, Willis Tower, and Field Museum. We would have saved money on admissions, and in fact we could not even get into the Shedd Aquarium because of the line (CityPASS holders had express entry). 

Mentioned in this answer:

  1. Willis Tower (attraction)
  2. Shedd Aquarium (attraction)
2 thankscomments (1)

answered by
Christy from Seven Hills

I visited Chicago twice last year with my husband. Not sure how you are getting there but if you are driving or are thinking of renting a car, just be aware that parking costs are pretty high. It's probably cheaper to take cabs or public transportation.

We didn't do everything on your tentative itinerary, but we did see The Field Museum, Willis Tower (formerly Sears Tower), Millennium Park, Loop, Magnificent Mile, Chicago Cultural Center, the former Marshall Field's (now a Macy's) and walked down by the river ( Chicago Riverwalk). We also went to the Shedd Aquarium, Adler Planetarium, Museum of Science and Industry (MSI), and took an architectural boat tour and a segway tour.  Of everything we did during our trips, the only thing I'd recommend not doing is the Adler Planetarium (I just felt it was more geared towards kids than adults).  

If you think you'd be interested in the aquarium and the MSI or John Hancock Observatory, check out the City Pass.

I highly recommend the Chicago Instagreeter tours. They are free guided one hour tours that depart from the Cultural Center. We took the Loop tour and the Millennium Park tour, and enjoyed both. During the Loop tour, we first were able to see the ceiling of the Cultural Center, and later were taken into the former Marshall Fields and were able to see that ceiling as well. They also offer longer free guided tours through that site, but you need to reserve those in advance. The instagreeter tours are first come, first serve. 

Of everything we did during our trips, my favorites were the walking tours, the boat tour, the segway tour, the Field Museum and visiting the River Walk.

The following are restaurants we ate at that I'd recommend:

Quartino -- Quartino

La Madia -- La Madia 

Sable Kitchen & Bar -- Sable 

XOCO -- Xoco (quick Mexican food)

Yolk -- Yolk (awesome breakfasts)

Wildberry Pancakes & Cafe -- Wildberry Pancakes & Cafe (awesome breakfasts; get there early to avoid a big wait)

If you are interested, I blogged our first Chicago trip here and here.

Enjoy your trip! 

Mentioned in this answer:

  1. The Field Museum (attraction)
  2. Willis Tower (attraction)
  3. Millennium Park (attraction)
  4. Loop (attraction)
  5. Magnificent Mile (attraction)
  6. Chicago Cultural Center (attraction)
  7. Macy's (attraction)
  8. Chicago Riverwalk (attraction)
  9. Shedd Aquarium (attraction)
  10. Adler Planetarium (attraction)
  11. Museum of Science and Industry (attraction)
  12. John Hancock Observatory (attraction)
  13. Quartino (restaurant)
  14. La Madia (restaurant)
  15. Sable Kitchen & Bar (restaurant)
  16. XOCO (restaurant)
  17. Yolk (restaurant)
  18. Wildberry Pancakes & Cafe (restaurant)
1 thankscomments (1)

answered by
Tommy from Chicago

Chicago Architecture Foundation River Cruise first it will give you a nice clarification of your whereabouts. This will last 2-3 hours from there you can walk south down   Michigan Avenue to the Cultural Center. After checking that place out you could walk across the street to  Millennium Park Depending on the day of the week you might be able to catch a live concert or orchestra at the park. If you want to knock out a few things at once you can go to   The Art Institute of Chicagowhich is right next to Millennium Park.  

Jump on the Blue Line towards O'hare and get off on the Belmont stop. You're in the Polish Village, check out the sites on Milwaukee avenue, and then head east and it at Kuma's Corneror  Hot Doug's these are the best Hamburger, and Hot Dog places in Chicago. Jump back on the Blue Line to transfer to the Red Line then head to the Chinatown stop. If you want to eat there I'd recommend  Three Happiness

You like to put some creative thought behind this romantic trip. Give your lady the book "Devil in the White City" it's a little dark but very thrilling and historical to Chicago. Then when you come you can see  The Field Museum you can see the exhibit the World's Fair artifacts. Then if you are bicyclists and have the chops to ride about 20 miles round trip, you can rent some bikes. And ride the Bike path all the way to Hyde Park. Things to see there  University of Chicago the  Rockefeller Chapel. Oh and you want some romance go to the  Osaka garden. Also go to Museum of Science and Industry so you can see one of the original buildings and the layout of the Devil in the White City. Then you can ride the bike path back down town. If you can handle those 20 miles on a bike you can also ride the bike path north to Wrigley Field.

You want some must sees.  Second City great place for night entertainment and see future SNL cast members every night there. The  The Rookery building designed by Daniel Burnham. A walk near the lake and  Buckingham Fountainat night adds to the city of Chicago romantic factor. If you want to get nostalgic you can take the Red Line to Lawrence stop and got to the The Green Mill for live jazz that will take you back to the Al Capone era of Chicago.

 If you want some quality local date places that are not to expensive here you go. These places will help you escape the hustle and bustle of the big city, but be romantic enough and affordable to be unforgettable. 

Rose Angelis

A Tavola



Mentioned in this answer:

  1. Chicago Architecture Tour (attraction)
  2. Chicago Architecture Foundation River Cruise (attraction)
  3. Chicago Architecture Tour (attraction)
  4. Michigan Avenue (attraction)
  5. Millennium Park (attraction)
  6. The Art Institute of Chicago (attraction)
  7. Kuma's Corner (restaurant)
  8. Hot Doug's (restaurant)
  9. Three Happiness (restaurant)
  10. The Field Museum (attraction)
  11. University of Chicago (attraction)
  12. Rockefeller Chapel (attraction)
  13. Osaka garden (attraction)
  14. Museum of Science and Industry (attraction)
  15. Second City (attraction)
  16. The Rookery (attraction)
  17. Buckingham Fountain (restaurant)
  18. The Green Mill (attraction)
  19. Rose Angelis (restaurant)
  20. A Tavola (restaurant)
  21. Homestead (attraction)

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