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In Chicago for 2 nights, what should I do?

I'll be in Chicago with my wife for 2 nights over the 4th of July and I'm looking for recommendation on hotels, restaurants, and things to do.  I'm thinking we want to stay right downtown but I could be convinced otherwise.  We want to see a Cubs game, and are considering the Architecture boat cruise? Where should I eat and drink? What's our best bet for fireworks? Cubs game - rooftop or stadium? Is the Architecture cruise worth it? What other must see things should we consider?

6 Answers

top answer by
Lauren from Chicago

Hi Shayne-

First off, I would definitely do the Architecture Boat Cruise-totally worth it! I would try and stay somewhere in River North - it's right in the thick of things and easy access to the Red Line (subway) that can drop you off right at Wrigley Field's doorstep. I would skip the rooftop and go to the stadium, it gives you a more authentic feel for the game and the stadium, in my opinion.

As for fireworks, it's obviously going to be pretty crazy. You can find a seat in the grass along the lake near Monroe Harbor, but, like Navy Pier, people get their early to stake their claim. The view from the grassy area near Adler Planetarium would also be a good spot. You could also try and get a spot at the The J. Parker, a rooftop bar in Lincoln Park, or at the The Terrace at Trump on the 90th floor of Trump Tower. Both of these rooftops would offer stunning views of the fireworks, but I'd definitely try and get a reservation if possible because others know about these prime spots as well.  Another option is to book a fireworks boat cruise from Navy Pier and see the fireworks from the water-the boats get pretty close and you get a great view. 

Chicago has endless food options so if you're looking for a particular type of cuisine or atmosphere let me know and I'd be happy to offer more specific recommendations. GT Fish & Oyster (seafood), Siena Tavern(Italian), Frontera Grill(Mexican), Beatrix (breakfast or brunch, coffee and pastries), Tanta Chicago(Peruvian), Bavette's Bar and Boeuf(steak), and Oak+Char (small plates, American) are just a few of many great restaurants in that area. If you want some of the best doughnuts in the country head to Doughnut Vault-just make sure to get there early because there will be a line forming even before they open. 

Have fun in Chicago, let me know if you have any other questions!

Mentioned in this answer:

  1. River North (neighborhood)
  2. Wrigley Field (attraction)
  3. Monroe Harbor (attraction)
  4. Adler Planetarium (attraction)
  5. The J. Parker (restaurant)
  6. The Terrace at Trump (restaurant)
  7. GT Fish & Oyster (restaurant)
  8. Siena Tavern (restaurant)
  9. Frontera Grill (restaurant)
  10. Beatrix (restaurant)
  11. Tanta Chicago (attraction)
  12. Bavette's Bar and Boeuf (restaurant)
  13. Oak+Char (restaurant)
  14. Doughnut Vault (restaurant)
  15. Navy Pier (attraction)
4 thankscomments (1)

answered by
Gerry from Boston

I always stay at Club Quarters, located at Wacker and Michigan Ave.

A great little hotel, very clean, very reasonably priced,  surrounded by all kinds of great restaurants and pubs. The river cruises are across the street.

You`re right in the middle of everything!!!

Mentioned in this answer:

  1. Club Quarters (hotel)
2 thanks

answered by
Hazel from Port St. Lucie

Architecture Cruise off the Navy Pier, also lots of other boat options there. The Signature Room at the 95th. Rent Bikes along the Lakeshore. 

Mentioned in this answer:

  1. The Signature Room at the 95th (restaurant)
  2. Navy Pier (attraction)
2 thanks

answered by
Jillian from Los Angeles

Hi Shayne!

I lived there for 8 years and Chicago summers are THE best!

Hotels - I'd recommend staying at the Hotel Palomar Chicago or for a splurge The James Chicago Hotel. Both are located in River Northand will give you endless options for walking and hopping the red line to Wrigley Field (I'd recommend public transportation on game days to avoid traffic) for a Cubs game. I'd also go for the stadium over rooftop if it's your first Cubs game - maybe even look for some bleacher tickets! 

Restaurants - my favorites are Au Cheval for their cheeseburger with egg on top, GT Fish & Oyster for their oysters, and Ada Street which is a hidden gem with great cocktails and delicious food in Lincoln Park. I also love Longman & Eagle, an amazing Michelin star place in Logan Square if you want to venture out of River North. You also can't go wrong with Gilt Bar or nearby Bavette's Bar and Boeuf. Great atmosphere and delicious food at both. You could also get a drink at The Signature Room at the 95th, a little touristy, but fun.

I'd also recommend taking a walk one morning to Lake Michigan, maybe walk Michigan Avenue to Oak Street Beach and head to North Beach for a great view of the city.  

Another thing you might consider is going to see Grateful Dead at Soldier FIELD. Not sure if that interests you at all, but they are playing July 3rd, 4th, and 5th!

Have fun, let me know if you have any other questions. Happy to help as much as I can.

Mentioned in this answer:

  1. Hotel Palomar Chicago (hotel)
  2. The James Chicago Hotel (hotel)
  3. River North (neighborhood)
  4. Wrigley Field (attraction)
  5. Au Cheval (restaurant)
  6. GT Fish & Oyster (restaurant)
  7. Ada Street (restaurant)
  8. Longman & Eagle (restaurant)
  9. Logan Square (attraction)
  10. Gilt Bar (restaurant)
  11. Bavette's Bar and Boeuf (restaurant)
  12. The Signature Room at the 95th (restaurant)
  13. Lake Michigan (attraction)
  14. Oak Street Beach (attraction)
  15. North Beach (attraction)
  16. Soldier FIELD (attraction)
2 thankscomments (2)

answered by
Dabs from Chicago

Agree with Lauren, stay in River North or just south of the River along Michigan Avenue.  Also agree about getting tickets inside the stadium and that the Architecture cruises are great as long as the weather is good.  For the best architectural information, the ones run by the Chicago Architecture Foundation Chicago's First Lady are widely thought to be the best, otherwise, you could also go on Wendella Boats or Shoreline Sightseeing which has pickups at Navy Pier and also at Michigan & Wacker.  Some go out on the Lake, some just on the River, and some go on both, all are good.  You can also take a Shoreline Water Taxi all the way to Chinatown and then take the el back.

So hard to recommend restaurants without any idea or budget or preferences, there are a ton of great restaurants in almost every imaginable cuisine in all kinds of price ranges.  Lots of people come for the pizza, I'd recommend Giordano's Pizza for stuffed or Lou Malnati's Pizzeria for deep dish.  Others come for the steakhouses, my personal favorite is Morton's The Steakhouse, I also like Wildfire.  For seafood, Joe's Seafood, Prime Steak & Stone Crab.  But there are dozens and dozens of good restaurants that neither one of us has mentioned.

Mentioned in this answer:

  1. Chicago's First Lady (attraction)
  2. Wendella Boats (attraction)
  3. Shoreline Sightseeing (attraction)
  4. Shoreline Water Taxi (attraction)
  5. Giordano's Pizza (restaurant)
  6. Lou Malnati's Pizzeria (restaurant)
  7. Morton's The Steakhouse (restaurant)
  8. Wildfire (attraction)
  9. Joe's Seafood, Prime Steak & Stone Crab (restaurant)
  10. Navy Pier (attraction)
2 thankscomments (1)

answered by
Peter from Springfield, Illinois

Go to the Skydeck Chicago in willis tower!

Mentioned in this answer:

  1. Skydeck Chicago (attraction)

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