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
27
28
29
30
31
1
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
30

Chicago — 28 nights

Windy City

Get out of town with these interesting Chicago side-trips: South Bend (Grotto of Our Lady Lourdes, Basilica of the Sacred Heart, &more), Centennial Bike Trail (in Willow Springs) and Milwaukee (City Hall, Ray's The Limit Charters, &more). There's still lots to do: explore the world behind art at The Art Institute of Chicago, take in panoramic vistas at 360 Chicago Observation Deck, don't miss a visit to Skydeck Chicago - Willis Tower, and stroll around Millennium Park.

For traveler tips, ratings, where to stay, and tourist information, read our Chicago itinerary maker website.

If you are flying in from Denmark, the closest major aiports are Chicago Midway International Airport, Chicago O'Hare International Airport and Gary Chicago International Airport. In September, plan for daily highs up to 30°C, and evening lows to 19°C.
more
Parks · Historic Sites · Museums · Outdoors
Side Trips