Chicago – An Apple a Plane https://anappleaplane.com Learn how to travel the world on a budget as a full time teacher or other 9-5 professional! Tue, 10 Mar 2026 03:04:44 +0000 en-US hourly 1 https://wordpress.org/?v=6.9.4 https://anappleaplane.com/wp-content/uploads/2021/01/Logo-150x150.png Chicago – An Apple a Plane https://anappleaplane.com 32 32 10 Things To Do in Chicago Over Memorial Day Weekend [2026] https://anappleaplane.com/chicago-memorial-day-weekend/?utm_source=rss&utm_medium=rss&utm_campaign=chicago-memorial-day-weekend Tue, 10 Mar 2026 03:04:41 +0000 https://anappleaplane.com/?p=8645 Are you looking for the best things to do in Chicago over Memorial Day Weekend?  This is the guide for you! Memorial Day Weekend in Chicago in 2026 is Friday, May 22, through Monday, May 25. The long weekend marks the unofficial start of summer in the city. Beaches reopen, neighborhood street festivals return, and […]

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]]> 15 Non-Touristy Things To Do in Chicago (Hidden Gems Locals Love) [2026] https://anappleaplane.com/non-touristy-things-to-do-in-chicago/?utm_source=rss&utm_medium=rss&utm_campaign=non-touristy-things-to-do-in-chicago Wed, 18 Feb 2026 02:48:04 +0000 https://anappleaplane.com/?p=7650 Looking for the best non-touristy things to do in Chicago?  This is the guide for you!  As a Midwest local, I’ll take you through the city’s gems that many visitors tend to miss. Chicago is full of iconic sights, but the city’s real character shows up in its hidden corners. From tucked-away art galleries to […]

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]]> 10 Amazing USA Labor Day Weekend Trips [2026] https://anappleaplane.com/labor-day-weekend-trips/?utm_source=rss&utm_medium=rss&utm_campaign=labor-day-weekend-trips Wed, 18 Feb 2026 02:33:55 +0000 https://anappleaplane.com/?p=6950 Looking for the best Labor Day weekend trips in the USA for 2026? This guide highlights destinations that shine during the long weekend — complete with seasonal events, ideal weather, and late-summer energy. Labor Day Weekend 2026 falls on September 5–7, marking the unofficial end of summer. It’s the perfect time to plan one last […]

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]]> What to Wear in Summer in Chicago: The Ultimate Packing List [2026] https://anappleaplane.com/summer-in-chicago-packing-list/?utm_source=rss&utm_medium=rss&utm_campaign=summer-in-chicago-packing-list Thu, 05 Feb 2026 01:40:03 +0000 https://anappleaplane.com/?p=8643 Are you searching for what to wear in Chicago this summer?  This ultimate packing list has got you covered! I spend tons of time in the city during all seasons of the year, and I completely have your back.  This list is based on personal experience and created with a carry-on-friendly mindset. Summer in Chicago […]

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]]> 12 Best Summer Vacations in The Midwest [2026] https://anappleaplane.com/summer-vacations-midwest/?utm_source=rss&utm_medium=rss&utm_campaign=summer-vacations-midwest Thu, 05 Feb 2026 01:12:17 +0000 https://anappleaplane.com/?p=6628 Looking for the best summer vacations in the Midwest?  This 2026 guide has you covered with travel ideas perfect for all kinds of travelers — from city lovers to waterfall chasers. The Midwest United States refers to the states in the middle of the country, including Illinois, Indiana, Iowa, Ohio, Missouri, and more.  I’ve spent […]

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]]> 8 Spring Things To Do Outdoors in Chicago [2026] https://anappleaplane.com/spring-things-to-do-in-chicago/?utm_source=rss&utm_medium=rss&utm_campaign=spring-things-to-do-in-chicago Wed, 04 Feb 2026 02:06:11 +0000 https://anappleaplane.com/?p=8309 Looking for the best spring things to do outdoors in Chicago in 2026? This is the guide for you! I love visiting Chicago in the spring — from the tulips blooming along Michigan Avenue to the peaceful vibes of Ping Tom Memorial Park, the city begins to come alive after winter. With longer days and […]

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]]> What To Wear in Winter in Chicago: The Ultimate Packing List [2026] https://anappleaplane.com/what-to-wear-in-winter-chicago-packing-list/?utm_source=rss&utm_medium=rss&utm_campaign=what-to-wear-in-winter-chicago-packing-list Wed, 28 Jan 2026 01:33:02 +0000 https://anappleaplane.com/?p=7316 Looking for what to wear in Winter in Chicago?  This is the guide for you! Visiting Chicago in winter can be a magical experience, with snow-dusted landmarks and festive lights illuminating the city. However, to fully enjoy your trip, it’s crucial to pack wisely for the biting cold and swirling winds. Chicago is known for […]

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]]> 8 Things To Do in Lakeview Chicago [2026] https://anappleaplane.com/things-to-do-in-lakeview-chicago/?utm_source=rss&utm_medium=rss&utm_campaign=things-to-do-in-lakeview-chicago Tue, 02 Dec 2025 13:40:00 +0000 https://anappleaplane.com/?p=7730 Looking for the best things to do in Lakeview, Chicago?  This detailed guide has got you covered! Lakeview is one of Chicago’s North Side neighborhoods.  It’s unique because it is comprised of several smaller sub-neighborhoods like Wrigleyville, known for the Chicago Cubs.  I have spent so much time in Lakeview with friends. Lakeview is laid-back […]

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