I went to Chicago with 3 of my childhood friends and it was the first time in Chicago for 3 out of the 4 of us. This was one of the quicker trips I have ever taken -- we were there a little over 48 hours. Still, I would rank Chicago as one of the best cities I have ever visited, especially for a quick weekend trip. The phrase "Chicago Summers" is completely true -- a great city to visit when the weather is warmer because of the beach access, great restaurants, and city feel with an affordable budget.

Day 1: Inbound Flight + Tourist Activities

• Take an inbound Spirit flight early in the morning from LGA to ORD and arrive by 8 AM

• Use the train to get into the city center because it is faster and cheaper

• Take pictures at The Bean

• Leave backpacks at the hotel

  • We lived at the Embassy Suites by Hilton in River North which was in a great location and they give you free breakfast and drinks to use at their bar

• Head to Pequod's Pizza to try Deep Dish -- definitely reserve this in advance

  • I am a NYC kid at heart, but I was pleasantly surprised by how much I did like deep dish

• Go straight to Wrigley Field for a tour of one of the most historic ballparks -- book in advance

• Head back to the hotel area and shop around while waiting for the room to be ready

• Head to dinner at avec

  • A restaurant featured in The Bear that was phenomenal as far as Middle Eastern/Mediterranean food goes

• Check out the LH Rooftop and then wind down the rest of the night by walking along the Riverwalk and bar hopping the stalls they have set up with drinks

Day 2: More Tourist Activities + Going Out

• Walk to the Ohio Street Beach to see the immense coastline of Chicago along the lake

• Walk through the entire Navy Pier and get lunch there

• Head to Portillo's to eat a famous hot dog and then walk the Magnificent Mile

• Try a flight at the Starbucks Reserve as an early evening drink

• Eat dinner at ROOH and walk to the bars after

• Federales Fulton has ice shots that you then throw at a bell to get it to ring

  • Total tourist trap but I was the only one that got the sound so it was totally worth it

• Bar hop the rest of the night

Day 3: More Good Eats + Return

• Sleep in and then go to Wildberry for brunch

  • We did not know how popular this place was going to be and did not reserve -- it looks very good and I would try to eat here if possible

• Post up at a sports bar to watch football until it's time to head to the airport for the return flight