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Cleveland, Chicago

Can't decide! What's a better place to visit, Cleveland or Chicago?

Travelling in early September with an active one year old and two parents who are lovers of food, beer (drinks in general), museums, shopping and walking. 

We're stuck between Chicago and Cleveland - Which one do you recommend?

17 Answers

top answer by
Vince from Sarasota

No comperison; definately Chicago.

Chicago has a beautiful skyline and so much to do and see.

Stay near N Michigan Ave and can walk to Millennium Park where thy have free shows and concerts. Take a river cruise on the Chicago River.

Go on top of the Willis Tower (old Sears) tower. Visit the Museum of Contemporary Art, the Museum of Science and Industry, the Shedd Aquarium, etc.

Chicago has the best restuarants in the world and you must try the deep dish at Pizzeria UNO or Pizzeria Due or at Lou Malnati's Pizzeria. Also try their famous Italian Beef.

Great shopping on MIchigan Ave. and great bars and rsuarant on Rush St.


Mentioned in this answer:

  1. Chicago (city)
  2. N Michigan Ave (attraction)
  3. Millennium Park (attraction)
  4. Willis Tower (attraction)
  5. Museum of Contemporary Art (attraction)
  6. Museum of Science and Industry (attraction)
  7. Shedd Aquarium (attraction)
  8. Pizzeria UNO (restaurant)
  9. Pizzeria Due (restaurant)
  10. Lou Malnati's Pizzeria (restaurant)
4 thanks

answered by
Kimberly from Chicago

They are so different. I'm from Cleveland and live in Chicago. Cleveland has great museums: The Cleveland Museum of ArtCleveland Museum of Natural HistoryNegative SpaceCleveland Institute of ArtMuseum of Contemporary Art ClevelandGreat Lakes Science Center, and my favorite, Rock and Roll Hall of Fame and Museum.

Here are a few others:

And lots of information on TripAdvisor:

The Chicago list is huge: I don't even know where to begin. Tons of museums: My favorites: Museum of Contemporary ArtThe Art Institute of ChicagoMillenium Park, The BeanShedd AquariumField Museum of Natural HistoryAdler Planetarium.

In Chicago, there are great live music: SchubasLincoln HallThe Hideout, Andy's Jazz ClubThe Green Milland theatre venues: Steppenwolf TheatreBroadway in ChicagoMusic Box TheatreThe Chicago TheatreCadillac Palace Theatre.

Cleveland music venues: The Beachland Ballroom & TavernBarking Spider TavernGrog ShopNautica Pavilion

Both cities have amazing restaurants. It depends on your taste. I'm happy to recommend some great restaurants. Here's a start:

My favorite Cleveland restaurants: The Greenhouse Tavern, LolaLolitaTommy'sGamekeeper's TaverneUmami Asian KitchenFire Food & DrinkNighttownShuheiOtani Japanese RestaurantHunan CoventryHunan By the FallsHunan SolonRick's CafeBurntwood TavernBurntwood Tavern, and Paladar Latin Kitchen and Rum BarSérgio's SaraváSergio's in University Circle, Brio Tuscan GrilleBRAVO! Cucina ItalianaJoey's RestaurantYours Truly RestaurantYours Truly RestaurantCorky and Lenny'sJack's Deli and RestaurantThe Tavern CompanyGeraci's restaurantWinking Lizard TavernWinking Lizard TavernWinking Lizard TavernPanini GrillCoventry Panini's GrillFirst WatchFirst WatchFirst Watch. There are probably more, but since I don't live there anymore, I don't keep up with all the new places. I do go home to visit and these are definitely my favorites today (with a few oldies in there).

One of my favorite Chicago restaurants: Uncommon Ground or the other location Uncommon GroundLe Colonial ChicagoTanta ChicagoBeatrixRoy'sGirl & the GoatLula CaféThe Purple PigRJ GruntsButcher & The BurgerSmoque BBQDinosaur Bar-B-QueBub CityMon Ami GabiMindy's Hot ChocolateNomi RestaurantBurger Bar ChicagoNana90 Miles Cuban Cafe90 Miles Cuban CafeNextLou Malnati's PizzeriaLou Malnati's PizzeriaGino's EastCaro Mio Italian RistoranteRose AngelisDinottoRPM ItalianQuartinoPiccolo SognoCoco PazzoCoco Pazzo CafeMercadito ChicagoXOCOXOCOMercadito CounterMercadito KitchenAvecHarry's Velvet RoomHugo's Frog Bar & Fish HouseGibsons Bar & SteakhouseLOKaL, de ceroDMK Burger BarGrange Hall Burger Bar. There are so many more, but these are probably my top choices. There are a bunch of good restaurants on Hubbard St. and Fulton St. and on Randolph St. in the west loop (a few of which I mentioned). Too many to post.

Both cities have great sports and great venues for the major sports teams. Cleveland: 

Quicken Loans Arena

Progressive Field


United Center

Wrigley Field

Allstate Arena

Let me know if you need more recommendations based on your interests.

Mentioned in this answer:

  1. The Cleveland Museum of Art (attraction)
  2. Cleveland Museum of Natural History (attraction)
  3. Negative Space (attraction)
  4. Cleveland Institute of Art (attraction)
  5. Museum of Contemporary Art Cleveland (attraction)
  6. Great Lakes Science Center (attraction)
  7. Rock and Roll Hall of Fame and Museum (attraction)
  8. Museum of Contemporary Art (attraction)
  9. The Art Institute of Chicago (attraction)
  10. Millenium Park (attraction)
  11. The Bean (attraction)
  12. Shedd Aquarium (attraction)
  13. Field Museum of Natural History (attraction)
  14. Adler Planetarium (attraction)
  15. Schubas (attraction)
  16. Lincoln Hall (attraction)
  17. The Hideout (restaurant)
  18. Andy's Jazz Club (attraction)
  19. The Green Mill (attraction)
  20. Steppenwolf Theatre (attraction)
  21. Broadway in Chicago (attraction)
  22. Music Box Theatre (attraction)
  23. The Chicago Theatre (attraction)
  24. Cadillac Palace Theatre (attraction)
  25. The Beachland Ballroom & Tavern (restaurant)
  26. Barking Spider Tavern (restaurant)
  27. Grog Shop (attraction)
  28. Nautica Pavilion (attraction)
  29. The Greenhouse Tavern (restaurant)
  30. Lola (restaurant)
  31. Lolita (restaurant)
  32. Tommy's (restaurant)
  33. Gamekeeper's Taverne (restaurant)
  34. Umami Asian Kitchen (restaurant)
  35. Fire Food & Drink (attraction)
  36. Nighttown (restaurant)
  37. Shuhei (restaurant)
  38. Otani Japanese Restaurant (restaurant)
  39. Hunan Coventry (restaurant)
  40. Hunan By the Falls (restaurant)
  41. Hunan Solon (restaurant)
  42. Rick's Cafe (restaurant)
  43. Burntwood Tavern (restaurant)
  44. Burntwood Tavern (restaurant)
  45. Paladar Latin Kitchen and Rum Bar (restaurant)
  46. Sérgio's Saravá (restaurant)
  47. Sergio's in University Circle (restaurant)
  48. Brio Tuscan Grille (restaurant)
  49. BRAVO! Cucina Italiana (restaurant)
  50. Joey's Restaurant (restaurant)
  51. Yours Truly Restaurant (restaurant)
  52. Yours Truly Restaurant (restaurant)
  53. Corky and Lenny's (attraction)
  54. Jack's Deli and Restaurant (attraction)
  55. The Tavern Company (restaurant)
  56. Geraci's restaurant (restaurant)
  57. Winking Lizard Tavern (restaurant)
  58. Winking Lizard Tavern (restaurant)
  59. Winking Lizard Tavern (restaurant)
  60. Panini Grill (restaurant)
  61. Coventry Panini's Grill (restaurant)
  62. First Watch (restaurant)
  63. First Watch (restaurant)
  64. First Watch (restaurant)
  65. Uncommon Ground (restaurant)
  66. Uncommon Ground (restaurant)
  67. Le Colonial Chicago (restaurant)
  68. Tanta Chicago (attraction)
  69. Beatrix (restaurant)
  70. Roy's (restaurant)
  71. Girl & the Goat (restaurant)
  72. Lula Café (restaurant)
  73. The Purple Pig (restaurant)
  74. RJ Grunts (restaurant)
  75. Butcher & The Burger (attraction)
  76. Smoque BBQ (restaurant)
  77. Dinosaur Bar-B-Que (restaurant)
  78. Bub City (restaurant)
  79. Mon Ami Gabi (restaurant)
  80. Mindy's Hot Chocolate (restaurant)
  81. Nomi Restaurant (restaurant)
  82. Burger Bar Chicago (restaurant)
  83. Nana (restaurant)
  84. 90 Miles Cuban Cafe (restaurant)
  85. 90 Miles Cuban Cafe (restaurant)
  86. Next (restaurant)
  87. Lou Malnati's Pizzeria (restaurant)
  88. Lou Malnati's Pizzeria (restaurant)
  89. Gino's East (restaurant)
  90. Caro Mio Italian Ristorante (restaurant)
  91. Rose Angelis (restaurant)
  92. Dinotto (restaurant)
  93. RPM Italian (restaurant)
  94. Quartino (restaurant)
  95. Piccolo Sogno (restaurant)
  96. Coco Pazzo (restaurant)
  97. Coco Pazzo Cafe (restaurant)
  98. Mercadito Chicago (restaurant)
  99. XOCO (restaurant)
  100. XOCO (restaurant)
  101. Mercadito Counter (restaurant)
  102. Mercadito Kitchen (restaurant)
  103. Avec (restaurant)
  104. Harry's Velvet Room (restaurant)
  105. Hugo's Frog Bar & Fish House (restaurant)
  106. Gibsons Bar & Steakhouse (restaurant)
  107. LOKaL (attraction)
  108. de cero (restaurant)
  109. DMK Burger Bar (restaurant)
  110. Grange Hall Burger Bar (restaurant)
  111. Quicken Loans Arena (attraction)
  112. Progressive Field (attraction)
  113. United Center (attraction)
  114. Wrigley Field (attraction)
  115. Allstate Arena (attraction)
3 thanks

answered by
Jillian from Los Angeles

Hi Stephanie,

I may be biased because I'm from there--but I'd say go for Chicago! Chicago is a much bigger city than Cleveland, and if you love food, it's one of the best cities! I would recommend staying in River North or Gold Coast as both neighborhoods are very walkable to N Michigan Ave shopping and restaurants. Also, the bean at The Bean which is a must for your little one!

Some of my favorite food spots:

Au Cheval for the cheeseburger! Get an egg on top-- it's delish! They don't take reservations however, so I'd say get there right at 5pm when they open and you won't have a problem.

Pequod's Pizza - located a little outside of River North, but worth it! The caramelized crust is ON point! My favorite pizza closer to downtown would be Giordano's - they have multiple locations. Lou Malnati's Pizzeria is also classic. You can't go wrong with either for the deep dish Chicago style. If you like pineapple on your pizza, eater beware you won't find pineapple at Lou's.

Here's something that could be fun as well - what about a beer tour through the city? Check out - if you're up for it. :)

Please let me know if you have any specific follow up questions. Happy to help!

Mentioned in this answer:

  1. Chicago (city)
  2. River North (neighborhood)
  3. Gold Coast (neighborhood)
  4. N Michigan Ave (attraction)
  5. The Bean (attraction)
  6. Au Cheval (restaurant)
  7. Pequod's Pizza (restaurant)
  8. Giordano's (restaurant)
  9. Lou Malnati's Pizzeria (restaurant)
3 thanks

answered by
Susie from Chicago

Like Kimberly, I am from Cleveland but live in Chicago. Both cities have lots of options for beer, museums, shopping, and walking as she outlined already. Early September is a fantastic time to visit both cities. 

If you are in Cleveland September 5-7, there is an air and water show going on. There is a Jazz festival in Chicago September 3-6, if that helps tip the scale in either direction. 

I will say Cleveland is much more affordable, especially when it comes to accommodations and food, so you will likely get more for your money in Cleveland. The Art Museum in Cleveland is free, you only have to pay for special exhibits. 

The beer scene is superior in Chicago with Revolution, Half Acre, Goose Island, and Lagunitas. In nearby Indiana there is also 3 Floyds and 18th Street Brewery. If you do go to Chicago, you have to try Links Taproomwhich is an amazing beer bar with 30+ taps! However, Cleveland's Great Lakes, Fat Heads, and Akron's Hoppin' Frog all have some awesome beers and Winking Lizard (which Kimberly mentioned) is a fantastic beer bar and restaurant perfect for trying new beers. 

Walkability and shopping are much better in Chicago, but there are several great areas to stroll around Cleveland, such as the Ohio City where Goose Island and the historic West Side Market are. East 4th Street downtown has been really built up with restaurants, bars, and shops. On the east side near the art museum and Little Italy are also gems. There is also the Metroparks, which have miles of walking and biking trails.

I'm not sure if you were planning on flying or driving, but of course Cleveland is a lot closer to Ottawa if you plan to drive. Add on 5-6 more hours to get to Chicago. If you drive, you could easily stop in the Finger Lakes or Buffalo/Niagara Falls on your way. 

Good luck making the decision! 


Mentioned in this answer:

  1. Links Taproom (restaurant)
  2. West Side Market (attraction)
2 thanks

answered by
Hazel from Port St. Lucie

I love both!!! I go to both. Cleveland has much to see and do. Chicago has torn down a lot of old projects, leading the way for much building. If you don't mind congested traffic and expensive parking, then Chicago is the place for you. I was there two weeks ago. Fell and am recovering, watch out for uneven sidewalks. Cleveland has a beautiful downtown dining district, beautiful stadiums, etc.

Mentioned in this answer:

  1. Cleveland (city)
  2. Chicago (city)
1 thanks

answered by
MaryBeth from Los Angeles

Chicago.  No contest.  

1 thanks

answered by

Chicago- no contest ! Cleveland is interesting but not remotely on the same level.

Mentioned in this answer:

  1. Chicago (city)
  2. Cleveland (city)
1 thanks

answered by

Cleveland is boring. There's the Rock and Roll Hall of Fame and Museum and nothing much else to write home about. Chicago is one of the world's most exciting cities.  No comparison, quite honestly.

Mentioned in this answer:

  1. Cleveland (city)
  2. Rock and Roll Hall of Fame and Museum (attraction)
  3. Chicago (city)
1 thanks

answered first by
Curious from Detroit

Hands down - Its Chicago... Lot of option for fun, fun, nightlife, etc,.. 

Mentioned in this answer:

  1. Chicago (city)
1 thanks

answered by
Tom from Chicago

Chicago - to echo everyone else's sentiment here, it just isn't a contest. 

answered by
tristan from Defiance

I would say Chicago because there is a lot more things to do there and Cleveland is not the best compared to Chicago 

Mentioned in this answer:

  1. Chicago (city)

answered by
S. from Vancouver

Cleveland has a lot to offer in the way of food and beer and, particularly, culture, but it's a city of < 400,000 people whereas Chicago - also with food, beer, and culture - is a city of seven times that. Both have great art museums (admission to the The Cleveland Museum of Art is free) and world-class symphonies. You don't say how long your trip will be - more than two or three days in Cleveland might be too long. Chicago has the Field Museum of Natural History, which is notable. Cleveland has the great Cleveland Museum of Natural History. Chicago might be easier to fly to. Cleveland will be less expensive.

Mentioned in this answer:

  1. Cleveland (city)
  2. Chicago (city)
  3. The Cleveland Museum of Art (attraction)
  4. Field Museum of Natural History (attraction)
  5. Cleveland Museum of Natural History (attraction)

answered by
Stacey from Jackson, Mississippi

America has only 3 cities: New York, San Francisco & New Orleans. Everywhere else is Cleveland. - Tennesee Williams

answered by
Rockland from Chicago

Ugh. Is this some kind of joke? Chicago

Mentioned in this answer:

  1. Chicago (city)

answered by
Paige from Venice Beach

I have been to both several times and I recommend Chicago. There's a plethora of restaurants for pretty much any meal/drink you might be looking for and Chicago is definitely the best city for food lovers. There are several shops all along N Michigan Ave and also cool things to see such as the Shedd Aquarium, the Museum of Contemporary Art, The Bean, the Lincoln Park Zoo in Lincoln Park ect. You can walk all over the city and transportation is easy if you need to get somewhere a little farther out. (uber, the L, buses ect.)

Mentioned in this answer:

  1. Chicago (city)
  2. N Michigan Ave (attraction)
  3. Shedd Aquarium (attraction)
  4. Museum of Contemporary Art (attraction)
  5. The Bean (attraction)
  6. Lincoln Park Zoo (attraction)

answered by
Jennifer from Grayslake

I currently live in Chicago but have visited Cleveland many times. I must say, Cleveland is one of my favorite cities! I always eat at Lolawhich is one of Michael Symon's restaurants, and it is in the quaintest little area that you can walk around and explore. Cleveland has a big farm to table scene if that's your thing and I know you can find your share of craft beers and cocktails. I second what another person said about Cleveland being more affordable-this is for sure true although the public transportation will not be as good if you will be needing that. Chicago will have everything you need as everyone else has said, you will be better off not renting a car and making your way on foot-everything is pretty easy to find and public transportation if you need it is reliable. All of the food suggestions given are fantastic! There are so many events going on in September in Chicago if you are here September 4-7 I recommend making your way to Naperville it is an easy train ride for the Naperville Last Fling it's a family event with a parade, carnival rides, children’s area, music stages, and food vendors. This does fall on Labor Day so expect crowds but the river walk is gorgeous and there are little boutiques and restaurants as well. I hope you have a great time in whichever city you choose!

Mentioned in this answer:

  1. Lola (restaurant)
  2. Chicago (city)
  3. Naperville (city)

answered by
Will from Chicago

With your description, Chicago would be ideal for you.  

FOOD: Parents can try different food styles from different neighborhoods.  You have Chinatown Chicago, W Devon Ave (Indian and Pakistani), Greektown, River North (American and Chicago), and many others.  

BEER: Goose Island to try a "local" beer and there are plenty of rooftop bars for night out on the town

MUSEUMS: Museum Campus for several different museums in a walkable distance

SHOPPING: Magnificent Mile

WALKING:  Chicago Riverwalk and Navy Pier

KIDS: Millennium Park and Maggie Daley Park

Mentioned in this answer:

  1. Chinatown Chicago (attraction)
  2. W Devon Ave (attraction)
  3. Greektown (attraction)
  4. River North (neighborhood)
  5. Goose Island (restaurant)
  6. Museum Campus (attraction)
  7. Magnificent Mile (attraction)
  8. Chicago Riverwalk (attraction)
  9. Navy Pier (attraction)
  10. Millennium Park (attraction)
  11. Maggie Daley Park (attraction)

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