Spend a day in the Windy City without breaking the bank! Take this travel itinerary and personalize it to suit travel preferences and plans. This sample day is only about $80.
Start the day with Citrus and Gingersnap Pancakes at the Bongo Room for $10.25. The Bongo Room is known for their brunch and breakfast menu — they are so popular they no longer accept reservations.
Be sure to visit the Field Museum, a basic ticket costs $18 for adults with discounts for students and seniors. The museum focuses on science and history and holds the largest, most complete T. Rex fossil named Sue. Explore the Ancient Egypt exhibit and visit the Field Museum’s current exhibition as well.
Pick up lunch a Falafill while enjoying al fresco seating. This fresh, causal restaurant offers a picnic box for $9.50, which includes a complete meal of four falafels, an open pita, two sides and a dessert.
Peruse Millennium Park, an outdoor space filled with natural and cultural attractions. The space was converted from an industrial eyesore into a public cultural attraction with the help of Frank Gehry in 1997. The park includes gardens, landscape architecture and public art.
Dine at Delecce, an eclectic local restaurant. A dinner entrée, such as the Lobster Roll, and beverage will cost about $25. The restaurant is conveniently located near the next stop, Chicago’s Music Box Theatre.
Catch a movie at Chicago’s Music Box Theatre, known for its midnight screenings of cult classics, such as The Big Lebowski, and independent films. General tickets cost $10 and can be purchased in advance on the theatre’s website or at the box office.
Make a note of the most interesting parts of the trip and plan a return visit soon. For less than $100, Chicago is an affordable and eclectic option.
Read This Next
Top 5: Boutique Hotels in Chicago
North America
Oct 10, 2014All Reads on This Topic
Read Them All
#TrazeeTravel
Insta FeedDestinations / North America
Oct 22, 2026Stay in This Restored 1920s School Campus
In Fayetteville, West Virginia, you can now stay in what was once the town’s high school and middle school, thanks to the opening of Hill Hall Hotel. The 40-guestroom boutique property stretches out over the 1923 high school and Mid-Century middle school buildings, retaining some of the original architecture and layout, while updating amenities to meet modern travelers’ needs.
Sponsored Content
12 Reasons to Visit Gozo, Malta’s Slower Sister Island
Gozo may be small in size, but Malta’s charming sister island offers a unique blend of natural beauty, deep-rooted history, rich culture and adventure. Gozo offers unforgettable experiences for every type of traveler. From picturesque villages and cliffside views to ancient temples and festive celebrations, the island invites visitors to slow down and savor the true Mediterranean lifestyle.
6 Skincare Mistakes to Avoid Before and After a Flight This Winter
An airplane’s cabin is already dry, but add in the winter climate and your skin practically begs for help. This season, keep skin healthy and moisturized by avoiding these six common mistakes when traveling:
Destinations / Europe
Oct 21, 2026Ease Into Autumn with Anantara’s European Wellness Retreats
Anantara Hotels & Resorts welcomes travelers to an autumnal escape with a collection of wellness experiences across its European properties. From hot mindful yoga and meditation to signature treatments like a Monoi Oil Body Wrap, these immersive retreats let guests unwind and rejuvenate as the seasons fade into one another.
Sponsored Content
Extraordinary Moments, Made to Keep
The Excellence Collection offers a curated collection of luxurious resorts across Mexico and the Caribbean, promising exceptional experiences for every guest and taste. From upscale suite concepts to a plethora of gourmet dining options, from wellness experiences to curated activities, The Excellence Collection guarantees all this and more.
Surveys
Oct 21, 2026Business Travel Bigger Than Ever, According to New Hotels.com Study
While just a few years ago, the travel industry may’ve been worried about business travel returning to its pre-pandemic numbers, according to a new Hotels.com study, that worry is no more. Business travel is back — and even more, it’s busier than ever for some travelers.
ShareThis