29 days in Chicago Itinerary

29 days in Chicago Itinerary

Created using Inspirock Chicago itinerary builder

Make it your trip
1
Chicago
— 28 nights

S M T W T F S
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18

Chicago

— 28 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Take a break from the city and head to Little Red Schoolhouse and Prairie Wolf Slough. Visit Rosewood Beach and Silver Beach County Park for some beach relaxation. Change things up with these side-trips from Chicago: Chesterton (Coffee Creek Watershed Preserve & Cowles Bog), Swallow Cliff Stairs (in Palos Park) and Whihala Beach (in Whiting). Next up on the itinerary: wander the streets of The Magnificent Mile, contemplate the long history of Ernest Hemingway Birthplace, admire the striking features of Frank Lloyd Wright's Robie House, and take in the spiritual surroundings of Fourth Presbyterian Church.

To find traveler tips, maps, photos, and other tourist information, refer to the Chicago road trip planning site.

April in Chicago sees daily highs of 59°F and lows of 40°F at night. Wrap up your sightseeing on the 18th (Sat) to allow time to travel back home.

Things to do in Chicago

Parks · Wildlife · Outdoors · Trails

Side Trips