Weather keeping you grounded this season? These 4 tips can help you plan a holiday “staycation” in Chicago.


Weather keeping you grounded this season? These 4 tips can help you plan a holiday “staycation” in Chicago.

 

Sponsored by JPMorganChase

Holiday travel can be exciting, but winter weather, crowded airports and packed schedules can sometimes make the idea of staying at home much more appealing.

If you still want to get away without the hassle of an actual getaway, consider a holiday staycation.

By remaining close to home, you can experience Chicago from a fresh perspective without the stress of a long trip. Whether you book a night at a local hotel, check out a new neighborhood or just finally get around to seeing that landmark attraction that’s been on your to-do list, you can make staying at home feel like a real getaway.

Laurie Sutor a Travel Advisor with Chase Travel, shares 4 tips you can use to create an amazing holiday at home this season.

1. Treat your hometown like a destination

One common theme surrounding area attractions is that they’re more likely to be packed with tourists than locals. If that popular museum, tour or other institution is always “there,” it can be easy to avoid it and say you’ll get there eventually.

The pedestrian-friendly Museum Campus in Chicago offers multi-generational appeal through the Field Museum, Adler Planetarium, and Shedd Aquarium. Neighboring hotel guests hold a unique advantage: inclement weather thins out local commuter crowds, leaving the campus highly accessible to nearby tourists within walking distance.

Stepping boldly into the skyline of Chicago’s historic South Side, the newly opened Obama Presidential Center has officially arrived for the 2026 travel season, transforming Jackson Park into a breathtaking global beacon of hope, history, and community architecture

A staycation provides a great opportunity to approach those kinds of places in Chicago like a tourist. Start by making a short list of places or experiences you’ve always wanted to try but never seem to prioritize. You might include a neighborhood, or you might attend a holiday-related performance that’s an annual late fall or winter tradition in your area.

2. Spend the night away

A hotel stay can provide a change of scenery that makes you feel like you’re enjoying a getaway.

For families looking to embrace the crisp winter air, choosing a hotel within walking distance of Millennium Park places you at the epicenter of Chicago’s holiday magic. Guests can spend their days gliding along the traditional McCormick Tribune Ice Skating Rink or navigating the winding paths of the Maggie Daley Park Ice Skating Ribbon. Afterward, the surrounding glass-walled restaurants offer the perfect vantage point to warm up with a hot drink while watching the skaters below.

There is something truly magical about watching winter unfold from the warmth of a luxury hotel right along the Chicago River. Guests can immerse themselves in premium amenities, from world-class spa pampering and exclusive seasonal events to stunning views of the iconic skyline. It is the perfect cozy base for exploring the vibrant River North neighborhood, home to some of the city's top-rated dining destinations.

If you want a quieter, more relaxed experience, find a hotel “off the beaten path,” but still close to home, to enjoy the rhythms and sounds of nature.

3. Be flexible

If your schedule allows, plan your staycation for a weekday or less crowded period — like the days between Christmas and New Year’s Eve — rather than a peak weekend. Hotel rates in the middle of the week tend to be cheaper, and it might be easier to grab a restaurant reservation or performance tickets. Locations might be less crowded as well during the week, making it easier to get around.

The holiday season in Chicago officially arrives with the iconic Christkindlmarket, a beloved, admission-free village that transforms downtown’s Daley Plaza into a magical 16th-century German winter market. The air is perpetually sweet with the comforting scent of roasted chestnuts and fresh pretzels.

You may find that perfect gift or holiday ornament. This runs throughout the Festive Season so you might capture a mid-week hotel rate.

4. Try something new

Even if you think you’ve seen everything your hometown has to offer, there’s always something new to explore or discover.

Start out your Festive Season on Saturday, November 21 for this year’s Wintrust Magnificent Mile Lights Festival. The festival kicks off with Lights Festival Lane from 11 a.m. to 4 p.m. The evening tree-lighting parade steps off at 5:30 p.m., followed by a spectacular fireworks display at 7:30 p.m.

Chicago comes alive during the holidays, the perfect time to enjoy our world-class theater scene. You can experience the Joffrey Ballet's production of The Nutcracker at the Civic Opera House, or the magnificent staging of A Christmas Carol at the Goodman Theatre. For those traveling with little ones, enjoy Dr. Seuss's How The Grinch Stole Christmas! The Musical at the James M. Nederlander Theatre.

No trip to the Windy City is complete without a night of side-splitting laughter at The Second City, the legendary Old Town institution that has served as the definitive crown jewel of American sketch and improv comedy since 1959.

With a little creativity, you might find that Chicago offers everything you’d want in a holiday vacation. You can enjoy good food, new experiences and an escape from your daily routine — all right at home.

For more tips, visit https://www.chase.com/travel/guide

For informational/educational purposes only: Views and strategies described in this article or provided via links may not be appropriate for everyone and are not intended as specific advice/recommendation for any business. Information has been obtained from sources believed to be reliable, but JPMorgan Chase & Co. or its affiliates and/or subsidiaries do not warrant its completeness or accuracy. The material is not intended to provide legal, tax, or financial advice or to indicate the availability or suitability of any JPMorgan Chase Bank, N.A. product or service. You should carefully consider your needs and objectives before making any decisions and consult the appropriate professional(s). Outlooks and past performance are not guarantees of future results. JPMorgan Chase & Co. and its affiliates are not responsible for, and do not provide or endorse third party products, services, or other content.

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 © 2026 JPMorgan Chase & Co. 


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