Chicago Itinerary for Summer Travel

As Chicagoans we may be biased, but we truly cannot say enough about our wonderful city. We’ve traveled all over the world and we still continue to discover new adventures and fall more in love with Chicago. With the pandemic still looming, many travelers are looking towards domestic trips this summer. Chicago is the perfect city for summer travel. Enjoy our guide for a long weekend in Chicago.

Four Day Itinerary

Day 1: River and Rooftops

Beatnik on the River
Kayak on the Chicago River
Mag Mile
Rooftop bar view from London House

Day 2: Bike and Beach

  • Take a cab up north to grab breakfast at Chicago’s newest breakfast gem, Wake n’ Bacon
  • After breakfast, find the nearest Divvy station to rent a bike and hop on the Lake Shore path going south
  • Bike until you arrive at North Avenue Beach in Lincoln Park and spend some time sunbathing and swimming at the beach
  • Grab lunch at Shore Club on the beach (don’t forget to order a frose)
  • Bike across the overpass to the (free) Lincoln Park Zoo and walk through the Alfred Caldwell Lily Pool after
  • Head over the the J Parker rooftop for a drink with incredible views of the city
  • Grab dinner at Homeslice for amazing pizza and one of our favorite patios in the city with a casual, funky vibe
  • Finish your night with a comedy show at Zanies Comedy Club in Old Town
Wake n Bacon
Lake Shore Path
North Avenue Beach
Alfred Caldwell Lily Pool
Homeslice Patio

Day 3: Baseball and Bars

  • Indulge in a bottomless mimosa brunch at El Mariachi
  • Enjoy a Chicago Cubs game at Wrigley Field
  • Hop around Wrigleyvile afterwards to bar hop at some local favorites like Sluggers, the Cubby Bear, and many more down Clark Street
  • Walk a few blocks west to the Southport Corridor for dinner. A few of our favorites are Tuco and Blondie or Coda Di Volpe
Wrigley Field
Tuco & Blondie

Day 4: Fountains and Food

  • Make a reservation at Cindy’s for brunch to start your day with incredible views of the city
  • Walk through Millennium Park and visit the Buckingham Fountain
  • Explore the Art Museum or the Shed Aquarium
  • Head over to West Loop and grab some coffee at the Allis
  • Walk down Randolph street to shop local businesses
  • Have dinner at Cabra to enjoy some Peruvian food from one of Chicago’s favorites chefs, Stephanie Izard
  • After dinner, pop over to Joe’s Import for some wine or Bombo Bar for dessert
View from Cindy’s Rooftop
Millenium Park
Cabra Rooftop
Joe’s Import

Where to Stay

There is an overwhelming amount of hotels to stay in Chicago, but here are a few we would highly recommend:

  • Waldorf Astoria -Located in Gold Coast, near the lake
  • Godfrey -Located in River North with a great rooftop bar
  • London House -Located in the heart of the loop with a great rooftop bar
  • Renaissance -Also located in the heart of the loop with a great rooftop bar
  • Hotel Zachary -Located in Wrigleyville with a trendy restaurant and views of Wrigley Field

We hope you love Chicago as much as we do. Let us know what your favorite part of your stay was! If you have any more Chicago related questions, feel free to reach out and we would be happy to chat more about our city.

Published by happilyaway

We are a married couple living in Chicago, and we are obsessed with traveling (probably like you). Unlike many travel bloggers, we have no intention on quitting our jobs and traveling full time because we actually love our jobs (shocker- I know) and we have a sweet puppy that we can't bear to leave for for than 3 weeks at a time. This hasn't stopped us from making all of our travel dreams come true. We are excited to share our adventures with you and help show you how you too, can travel the world- even while working full time. Emilie & Chris

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