Planning a Weekend Trip to Chicago: Making the Most of 48 Hours

Chicago is one of the greatest American destinations. It has something for everyone and even returning visitors will find something new. However, if you only have a weekend to spare, don’t fret: you can still see the best of the city in 48 hours!

A Mellow Friday Evening

Nothing starts “vacation mode” better than letting loose. Head by train to Wicker Park, which is home to dozens of fabulous restaurants. Tacos are a local favorite and the best are at Big Star, Antique Taco, and Tierra Caliente.

big star tacos wicker park chicagoTacos al Pastor – Photo by Ramsess Salazar via

As you make your way through this hipster community, meander through galleries and boutiques. Be sure to leave room for dessert at a neighborhood bakery and cap off your night with a drink. There’s no shortage of dive bars, upscale cocktail lounges, wine bars, or live music venues.

The Best of Chicago on Saturday

Set your alarm on Saturday morning and head directly to the Magnificent Mile. Get your bearings from above at 360 Chicago and then walk from the Water Tower down to the Chicago River. If you’ve worked up an appetite from window shopping, detour off Michigan Avenue for a slice of Chicago’s iconic deep dish pizza. You’ll find the original at Pizzeria Uno or its nearby sister restaurant, Pizzeria Due.

After lunch, learn both about city history and incredible architecture by joining a boat tour of the city; if you can, choose  the longer route that includes a ride on the lake.

wendella boat tour chicagoWendella Architectural Boat Cruise – Photo by Abi Estrella via

You’ll see landmarks like Navy Pier and the Skydeck along the way. Once you’ve disembarked, walk through Millennium Park to see the infamous “Cloud Gate” sculpture. If you have time, you can also visit the Art Institute.

At night, let your personality shine through. Find tickets to Chicago events like professional sports games, world-famous improv comedy, live theatre, or head to the loop’s nightclubs.

Spending Sunday South of the Loop

A quick bus ride from downtown will take you to Chicago’s renowned museum campus. It’s best to get to the Shedd Aquarium early because it gets busy as the day goes on. Be mesmerized by the jellyfish and watch dolphins do tricks. When you need a break, simply pop over to Chinatown for dim sum, the original Sunday brunch. When you’re re-energized, say hi to Sue the tyrannosaurus rex in the Field Museum or learn something new about ancient Egypt before saying goodbye to Chicago.

field museum chicagoThe Field Museum – Photo by Jess-ice cream & permafrost via

Choose a Central Hotel

With so many great activities all over the city, location is everything when picking a hotel. I like to stay near Millennium Park for easy access to the El train and public buses. Restaurants are at your doorstep and you can walk to shopping, museums, and even the lake. For starters, look at theWit Chicago – a DoubleTree by Hilton Hotel, Hotel Monaco Chicago – a Kimpton Hotel, or other Chicago hotels.

No matter how you spend your weekend, you’ll leave with great memories and stories to share. One thing’s for sure: a weekend in the city will leave you longing to return!

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This post is part of the #HipmunkCityLove campaign, but all opinions remain my own.  You know I always love writing about Chicago! 

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Read more about Chicago in my Hipmunk Hotel Guides:

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Becky (#HipmunkCityLove)

#HipmunkCityLove Contributor at The Girl and Globe
The Girl and Globe has partnered with to explore some exciting travel destinations! All posts are written by Becky and all opinions remain mine. Check out all the posts in this series to plan your next trip!

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