22 days in Chicago Itinerary
Created using Inspirock Chicago trip planner
Start from...
1
Chicago
— 21 nights
End at...
Fri, Oct 7 - Fri, Oct 28
Edit
S | M | T | W | T | F | S |
---|---|---|---|---|---|---|
2
|
3
|
4
|
5
|
6
|
7
|
8
|
9
|
10
|
11
|
12
|
13
|
14
|
15
|
16
|
17
|
18
|
19
|
20
|
21
|
22
|
23
|
24
|
25
|
26
|
27
|
28
|
29
|
View full calendar
Chicago — 21 nights

Windy City
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.Get out of town with these interesting Chicago side-trips: Edwards Apple Orchard (in Poplar Grove), Kline Creek Farm (in West Chicago) and Historic Auto Attractions (in Roscoe). There's still lots to do: explore the world behind art at The Art Institute of Chicago, stroll around Millennium Park, get curious at Museum of Science and Industry, and enjoy breathtaking views from 360 Chicago Observation Deck.
To find where to stay, photos, ratings, and more tourist information, go to the Chicago trip itinerary planner.
Expect a daytime high around 65°F in October, and nighttime lows around 49°F.
Side Trips
Find places to stay Oct 7 — 28: