Explore: Chicago Trips

Discover great vacation ideas, cool trip itineraries, and interesting places to visit in these Chicago Trips.

Trip Blog Post by @michfritz07: Route 66 Road Trip | 11 days in Jun (itinerary, map & gallery)

11 days in Jun

Route 66 Road Trip

Trip Blog Post by @dleon3232: Chicago 2021 | 5 days in Oct (itinerary, map & gallery)

5 days in Oct

Chicago 2021

Trip Blog Post by @beccafeldhauser: Last part of our 1 month road trip 2021 | 3 days in Aug (itinerary, map & gallery)

beccafeldhauser

3 days in Aug

Last part of our 1 month road trip 2021

Trip Blog Post by @rodney_n: Chicago Downtown 2009 | 1 day in Jul (itinerary, map & gallery)

1 day in Jul

Chicago Downtown 2009

Trip Blog Post by @Anne00001: Chicago 2021 | 2 days in May (itinerary, map & gallery)

2 days in May

Chicago 2021

Trip Blog Post by @elecard43: Chicago 2019 | 3 days in Oct (itinerary, map & gallery)

3 days in Oct

Chicago 2019

Trip Blog Post by @ketzer333: Chicago & Wisconsin 2019 | 6 days in Jun (itinerary, map & gallery)

6 days in Jun

Chicago & Wisconsin 2019

Trip Blog Post by @Leuri: Chicago 2017 | 5 days in Oct (itinerary, map & gallery)

5 days in Oct

Chicago 2017

Trip Blog Post by @egoodwin: 4 Days in Chicago (2012) | 4 days in May (itinerary, map & gallery)

4 days in May

4 Days in Chicago (2012)

Trip Blog Post by @brklyner: Chicago Weekend Trip | 4 days in Nov (itinerary, map & gallery)

4 days in Nov

Chicago Weekend Trip

Trip Blog Post by @R.O.Y: Chicago 2023 | 1 day in Mar (itinerary, map & gallery)

1 day in Mar

Chicago 2023

Trip Blog Post by @karenramirezsuarez: Chicago 2022 🇺🇸 | 9 days in Nov/Dec (itinerary, map & gallery)

karenramirezsuarez

9 days in Nov/Dec

Chicago 2022 🇺🇸

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