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Chicago must sees in 2-3 days? Hotels, restaurants, etc...

I'm going to a wedding in Iowa in October and want to explore Chicago after. I've never been to Chicago and would love to spend 2-3 days. What are the major attractions, places to stay, restaurants? Any info is appreciated!!! Thank you.

6 Answers

top answer by
Jillian from Los Angeles

Hi Joanne,

Chicago is amazing - I'm sure you will love it. I lived there for 8 years (and grew up in the suburbs) and love going back to visit.

As a first timer, I would recommend staying in River North as it's close to some amazing restaurants and attractions. My top pick for location and clean rooms would be Hotel Palomar Chicago (cheapest, trendy option I've found) or The Westin Michigan Avenue Chicago.

A new hotel I really want to check out is Richard Branson's new Virgin Hotels Chicago. It looks amazing (maybe a bit pricer though).

As for restaurants, for oysters, I like GT Fish & Oyster. For Italian, try Eataly Chicago and for the best burger in town, check out Au Cheval. Reservations recommended when possible! 

For classic Chicago deep dish pizza, my favorite is Lou Malnati's Pizzeria, but for caramelized crust pizza and to get out of the city a little, go for Pequod's Pizza in Lincoln Park. You can easily hop the red line or take an Uber. 

As for attractions, I love going to and taking pictures at the bean in Millenium Park. You can walk Michigan Avenue (quite touristy though) after and check out the river too for some nice views. Another spot that might interest you is the Willis Tower where you can step out on a ledge 103 floors up! The views are pretty amazing from here. Here's one I took last time I was there:

October should be good weather, but definitely pack a coat as one day it can be in the 60s and the next in the 30s during fall months. You never really know.. but definitely colder than Florida :)


Mentioned in this answer:

  1. River North (neighborhood)
  2. Hotel Palomar Chicago (hotel)
  3. The Westin Michigan Avenue Chicago (hotel)
  4. Virgin Hotels Chicago (hotel)
  5. GT Fish & Oyster (restaurant)
  6. Eataly Chicago (attraction)
  7. Au Cheval (restaurant)
  8. Lou Malnati's Pizzeria (restaurant)
  9. Pequod's Pizza (restaurant)
  10. Millenium Park (attraction)
  11. Michigan Avenue (attraction)
  12. Willis Tower (attraction)
5 thankscomments (2)

answered by
Dabs from Chicago

Be careful with October, the weekend of October 11th is the marathon weekend, hotel prices go through the roof and Italian restaurants are packed with carbo loaders.

River North is a great place to stay and the Magnificent Mile and Loop are also fine.  I tell people to stay as close to Michigan Avenue as possible, better access to the el and buses and more people about.

If the weather is nice, go for a boat ride on the river or lake.  Check out Millennium Park.  Go to the The Signature Lounge at the Hancock and have a drink and a great view.  If the weather is not so nice, there are great museums-the Art Institute, the Field Museum, the Shedd Aquarium, the Museum of Science and Industry (not in central downtown but you can get there by public transport) and several others depending on your interests.

Chicago has great dining ranging from hot dogs and pizza to Michelin starred restaurants.  It's really helpful when people give an idea of what they like and what their budget is.  If you want really high end dining, Alinea is consistently ranked as one of the top restaurants in the country.  If you want Chicago style pizza, I'd suggest Lou Malnati's Pizzeria or for stuffed Giordano's Pizza.  Hot dogs, Portillo's.  For steaks my go to places are Morton's The Steakhouse and Wildfire.  For seafood Joe's Seafood, Prime Steak & Stone Crab or Shaw's Crab House.  There are dozens and dozens of great ethnic places and lots of trendy places if that's your scene.

If you are here on the weekend of Oct 17-18, there is a great program called Open House run by the Chicago Architecture Foundation which gives access to many places that wouldn't normally be open.  It's one of my favorite weekends of the year

Mentioned in this answer:

  1. Millennium Park (attraction)
  2. The Signature Lounge (attraction)
  3. Alinea (restaurant)
  4. Lou Malnati's Pizzeria (restaurant)
  5. Giordano's Pizza (restaurant)
  6. Portillo's (restaurant)
  7. Morton's The Steakhouse (restaurant)
  8. Wildfire (attraction)
  9. Joe's Seafood, Prime Steak & Stone Crab (restaurant)
  10. Shaw's Crab House (restaurant)
4 thankscomments (3)

answered by
Lauren from Chicago

Hi Joanne,

I think Jillian and Kristi gave some great advice! River North is definitely a great place to stay, especially if it's your first time in Chicago, but being the main tourist hub makes it very expensive. If you're driving I would definitely look into the cost of parking/valet for your hotel so you can factor that into any budget you may have. If you're looking to save money and stay outside this area, just make sure you're near an El stop-from there it will be very easy to get anywhere in the city!

As far as food goes, Chicago is full of endless possibilities. Lou Malnati's Pizzeria and Pequod's Pizza are two of my favorites for deep dish pizza, and if you're on the north side closer to Wrigley FieldThe Art of Pizza might just be my favorite. Portillo's is another Chicago staple in River North where you can get a classic Chicago hot dog or beef sandwich and their famous chocolate cake shake. Below is a deep dish from The Art of Pizza :)

It's great to walk around Millennium Park, especially on a nice day. If you're into museums and/or art, The Art Institute of Chicago is one of the best in the world. For great views of the city, both the Willis Tower ($19.50) and Hancock Building ($19) have observation levels, but my favorite way to get my best bang for my buck is to go to the The Signature Lounge in the Hancock for a drink - you get the views of observation deck but your money goes towards overpriced cocktails rather than an admission fee. If you're their make sure to use the women's restrooms, oddly it has the best view! If you're near Lincoln Park, you can also grab a drink at the The J. Parker, a rooftop bar with more great views.

If the weather cooperates I would also highly recommend a Chicago Architectural Boat Tour - it's a unique way to see the city from below along the river and you get a ton of great of history at the same time.

For shopping, you'll find all the popular brands along Michigan Avenue, but if it's raining or you want everything in one place, Water Tower Place is where to go. 

For food I could go on and on, so if there's a certain type, price range, or location you're looking for just let me know! Brunch is big in Chicago on the weekends and GT Fish & OysterBohemian House, and Siena Tavern are great spots in the River North area, both for brunch and dinner. I also agree that stopping at Eataly Chicago is a must - even if it's not to eat, it's just a cool place to walk around. Shake Shack is right across the street for a quick lunch option and I also really love Rick Bayless' XOCO for a less formal meal. 

My all time favorite restaurant in Chicago is Bavette's Bar and Boeuf- definitely make reservations far in advance for them. AvecGirl & the GoatAu ChevalGreen Street Smoked MeatsCocelloOak+Char, and The Purple Pig are just a few of the many other great options in that general area. For drinks stop by Three Dots and a Dash for a fun tiki cocktail and for a sweet treat stop by the newly opened Amarino for beautiful gelato or Sprinkles Cupcakes for cupcakes. Here's a shot of the cheeseburger from Au Cheval -it's the best in the city in my opinion!

Chicago has some really great food tours as well - Chicago Food Planet has some great options and Chicago Pizza Tours will make sure you get your fill of deep dish. If you like craft beer, The Chicago Beer Experience has a great tour as well, or you could venture over to Lagunitas Brewing Company for a free tour and bite to eat in their brewpub.

Enjoy Chicago and if you need more recs for other neighborhoods let me know!



Mentioned in this answer:

  1. River North (neighborhood)
  2. Lou Malnati's Pizzeria (restaurant)
  3. Pequod's Pizza (restaurant)
  4. Wrigley Field (attraction)
  5. The Art of Pizza (restaurant)
  6. Portillo's (restaurant)
  7. Millennium Park (attraction)
  8. The Art Institute of Chicago (attraction)
  9. Willis Tower (attraction)
  10. Hancock Building (attraction)
  11. The Signature Lounge (attraction)
  12. Lincoln Park (attraction)
  13. The J. Parker (restaurant)
  14. Chicago Architectural Boat Tour (attraction)
  15. Michigan Avenue (attraction)
  16. Water Tower Place (attraction)
  17. GT Fish & Oyster (restaurant)
  18. Bohemian House (attraction)
  19. Siena Tavern (restaurant)
  20. Eataly Chicago (attraction)
  21. Shake Shack (restaurant)
  22. XOCO (restaurant)
  23. Bavette's Bar and Boeuf (restaurant)
  24. Avec (restaurant)
  25. Girl & the Goat (restaurant)
  26. Au Cheval (restaurant)
  27. Green Street Smoked Meats (restaurant)
  28. Cocello (restaurant)
  29. Oak+Char (restaurant)
  30. The Purple Pig (restaurant)
  31. Three Dots and a Dash (attraction)
  32. Sprinkles Cupcakes (restaurant)
  33. Lagunitas Brewing Company (restaurant)
3 thankscomments (2)

answered by
Pete from Indianapolis

If you are into Art at all, check out what the The Art Institute of Chicago is showing, and give yourself at least 3 hours to see it, if you do park downtown make sure you have moved your car by 5 (I think) because at a certain time they start towing all parked cars and getting it back is a nightmare. The Divvy Station: Ravenswood Ave & Berteau Ave bikes are fun to ride also.

2 thanks

answered by
Leonard from Minneapolis

Rick Bayless' trio of side-by-side restaurants are all fantastic. Frontera Grill, Topolobampo and fast-casual XOCO. Reservations are highly recommended for the first two, and Frontera may be the best of the three.

The best Chicago deep-dish is an argument that has been ignited family feuds and flame wars for generations  Lou Malnati's Pizzeria Giordano's and Gino's East are all local favorites.

Skydeck Chicago in the Willis Tower is a spectacular view, and if it wasn't facing the other way, you could probably see clear back to Iowa!

Untitled is one of the most unique nightclubs, done up as a speakeasy complete with an unmarked entry next to the CVS on Kinzie St.  Always a fun place to grab a cocktail!

Mentioned in this answer:

  1. Frontera Grill (restaurant)
  2. Topolobampo (restaurant)
  3. XOCO (restaurant)
  4. Lou Malnati's Pizzeria (restaurant)
  5. Giordano's (restaurant)
  6. Gino's East (restaurant)
  7. Skydeck Chicago (attraction)
  8. Untitled (attraction)
2 thanks

answered by

Mentioned in this answer:

  1. Millennium Park (attraction)
  2. Field Museum of Natural History (attraction)
  3. Aviary (restaurant)
  4. Next (restaurant)
  5. Girl & the Goat (restaurant)
  6. Three Dots and a Dash (attraction)
  7. Piece Pizzeria and Brewery (restaurant)
  8. Mercadito Chicago (restaurant)
  9. Half Acre Beer Company (restaurant)
  10. Mercat a la Planxa (restaurant)
1 thankscomments (1)

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