Roamly Destination Guide
Things to do in Chicago
A 5-day itinerary built from real traveler reviews — not ads.
Your 5-day Chicago itinerary
1
Day 1
- 08:00 Breakfast at Wildberry Pancakes and Cafe (Loop) — order the signature Wildberry pancakes; they're fluffy and packed with flavor, around $15.
- 10:00 Wrigley Field Tour (Wrigleyville) — a Roamly reviewer praised the knowledgeable guide and the chance to walk on the field, tickets are about $25.
- 12:30 Lunch at The Happy Camper (Wrigleyville) — try the pepperoni pizza with hot honey, a favorite among locals, around $40 per person.
- 14:30 Stroll through Lincoln Park — enjoy the greenery and visit the Lincoln Park Zoo, which is free and has a great variety of animals.
- 16:30 Visit the Chicago History Museum (Lincoln Park) — learn about Chicago's rich history; entry is $19.
- 18:30 Dinner at Lou Malnati's Pizzeria (Lincoln Park) — get the classic Chicago deep-dish pizza; a slice is about $5, and it’s a local favorite.
- 20:30 Evening walk along the Lakefront Trail — enjoy views of Lake Michigan and the city skyline.
2
Day 2
- 08:00 Breakfast at Beatrix (River North) — order the breakfast tacos; they’re packed with flavor, around $12.
- 10:00 Architecture River Cruise — a fantastic way to see the city's iconic buildings from the water; tickets are approximately $45.
- 12:30 Lunch at Portillo's (River North) — try the Chicago-style hot dog; it’s a local classic, around $10.
- 14:30 Explore Millennium Park — take photos with "The Bean" (Cloud Gate) and enjoy the beautiful gardens.
- 17:00 Visit the Art Institute of Chicago — home to countless masterpieces; entry is $25.
- 19:30 Dinner at The Purple Pig (Magnificent Mile) — order the bone marrow and the house-made sausage; tapas-style dining here can run about $30 per person.
3
Day 3
- 08:00 Breakfast at Egg Harbor Cafe (Lincoln Park) — try the French toast, around $12.
- 10:00 Visit the Field Museum — discover natural history; tickets are about $28.
- 12:30 Lunch at The Chicago Diner (Lakeview) — famous for its vegan shakes; try the Radical Reuben, around $15.
- 14:30 Explore Navy Pier — check out shops, and rides, and enjoy the waterfront views.
- 17:00 Visit the Shedd Aquarium — tickets are about $39; it's home to a fascinating array of marine life.
- 19:30 Dinner at Smoque BBQ (Logan Square) — order the brisket; it's highly rated for flavor and tenderness, around $25.
4
Day 4
- 08:00 Breakfast at Jasper's (West Loop) — order the breakfast burrito; hearty and delicious, around $10.
- 10:00 Explore Pilsen — check out the murals and visit the National Museum of Mexican Art, which is free.
- 12:30 Lunch at Carnitas Uruapan (Pilsen) — locals rave about the carnitas tacos, around $8.
- 14:30 Visit the Museum of Contemporary Art — entry is $15; the exhibits are thought-provoking.
- 17:00 Dinner at Al's Beef (Little Italy) — try the Italian beef sandwich; it’s a Chicago staple, around $10.
- 19:30 Catch a show at the Adler Planetarium — check their schedule for nighttime sky shows, tickets around $25.
5
Day 5
- 08:00 Breakfast at Bongo Room (Wicker Park) — order the chocolate caramel pretzel pancakes; they’re decadent, around $15.
- 10:00 Visit The Chicago Cultural Center — check out the stunning Tiffany glass dome and enjoy free art exhibitions.
- 12:30 Lunch at Manny’s Cafeteria & Delicatessen (Near South Side) — try the corned beef sandwich; it’s legendary, around $20.
- 14:30 Last-minute shopping on State Street — explore local stores and boutiques.
- 16:30 Enjoy a leisurely walk in Grant Park before heading to your departure point.
Top things to do in Chicago
- ✦Wrigley Field Tour
- ✦Architecture River Cruise
- ✦Art Institute of Chicago
- ✦Shedd Aquarium
- ✦Chicago Cultural Center
Where to eat in Chicago
- ●The Happy Camper
- ●Lou Malnati's Pizzeria
- ●Portillo's
- ●The Chicago Diner
- ●Smoque BBQ
- ●Carnitas Uruapan
Local tips most visitors miss
- ◆Pilsen Murals
- ◆Lincoln Park Conservatory
- ◆The Magic Parlour
- ◆Chicago Riverwalk
What travelers say about Chicago
Real reviews from people who've been — unsponsored.
The Happy Camper
I would highly recommend this place for anyone in Wrigleyville. The vibe of the place was funky and really cool. The drinks were awesome and the food was even better. My wife and I ended …
— Jacob
Wrigley Field Tour
As a baseball fan, this should be on everyone's list when visiting Chicago. It was really cool to see the history of the stadium and organization up close. On the tour you see the visitor's …
— Jacob
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