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A man and woman smile in front of the iconic red Flamingo sculpture in Chicago, Illinois, during a Signature City tour.
Illinois

Signature City Chicago

Program No. 2818RJ
Select Date
Weather by Date
2026
Signature City Chicago
Program No. 2818
09
Aug
BEGINS
Chicago, Illinois
14
Aug
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,399
Signature City Chicago
Program No. 2818
09
Aug
BEGINS
Chicago, Illinois
14
Aug
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,869
Signature City Chicago
Program No. 2818
09
Aug
BEGINS
Chicago, Illinois
14
Aug
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 4,798
Signature City Chicago
Program No. 2818
06
Sep
BEGINS
Chicago, Illinois
11
Sep
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,399
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
06
Sep
BEGINS
Chicago, Illinois
11
Sep
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,869
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
06
Sep
BEGINS
Chicago, Illinois
11
Sep
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 4,798
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
27
Sep
BEGINS
Chicago, Illinois
02
Oct
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,399
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
27
Sep
BEGINS
Chicago, Illinois
02
Oct
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,869
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
27
Sep
BEGINS
Chicago, Illinois
02
Oct
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 4,798
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
04
Oct
BEGINS
Chicago, Illinois
09
Oct
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,349
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
04
Oct
BEGINS
Chicago, Illinois
09
Oct
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,819
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
04
Oct
BEGINS
Chicago, Illinois
09
Oct
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 4,698
OR
Pay Deposit 100
2027
Signature City Chicago
Program No. 2818
11
Apr
BEGINS
Chicago, Illinois
16
Apr
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,449
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
11
Apr
BEGINS
Chicago, Illinois
16
Apr
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,949
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
11
Apr
BEGINS
Chicago, Illinois
16
Apr
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 4,898
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
02
May
BEGINS
Chicago, Illinois
07
May
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,499
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
02
May
BEGINS
Chicago, Illinois
07
May
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,999
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
02
May
BEGINS
Chicago, Illinois
07
May
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 4,998
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
16
May
BEGINS
Chicago, Illinois
21
May
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,499
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
16
May
BEGINS
Chicago, Illinois
21
May
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,999
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
16
May
BEGINS
Chicago, Illinois
21
May
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 4,998
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
30
May
BEGINS
Chicago, Illinois
04
Jun
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,499
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
30
May
BEGINS
Chicago, Illinois
04
Jun
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,999
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
30
May
BEGINS
Chicago, Illinois
04
Jun
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 4,998
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
20
Jun
BEGINS
Chicago, Illinois
25
Jun
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,499
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
20
Jun
BEGINS
Chicago, Illinois
25
Jun
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,999
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
20
Jun
BEGINS
Chicago, Illinois
25
Jun
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 4,998
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
11
Jul
BEGINS
Chicago, Illinois
16
Jul
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,499
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
11
Jul
BEGINS
Chicago, Illinois
16
Jul
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,999
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
11
Jul
BEGINS
Chicago, Illinois
16
Jul
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 4,998
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
29
Aug
BEGINS
Chicago, Illinois
03
Sep
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,499
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
29
Aug
BEGINS
Chicago, Illinois
03
Sep
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,999
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
29
Aug
BEGINS
Chicago, Illinois
03
Sep
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 4,998
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
05
Sep
BEGINS
Chicago, Illinois
10
Sep
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,499
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
05
Sep
BEGINS
Chicago, Illinois
10
Sep
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,999
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
05
Sep
BEGINS
Chicago, Illinois
10
Sep
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 4,998
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
19
Sep
BEGINS
Chicago, Illinois
24
Sep
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,499
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
19
Sep
BEGINS
Chicago, Illinois
24
Sep
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,999
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
19
Sep
BEGINS
Chicago, Illinois
24
Sep
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 4,998
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
03
Oct
BEGINS
Chicago, Illinois
08
Oct
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,499
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
03
Oct
BEGINS
Chicago, Illinois
08
Oct
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,999
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
03
Oct
BEGINS
Chicago, Illinois
08
Oct
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 4,998
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
17
Oct
BEGINS
Chicago, Illinois
22
Oct
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,499
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
17
Oct
BEGINS
Chicago, Illinois
22
Oct
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 2,999
OR
Pay Deposit 100
Signature City Chicago
Program No. 2818
17
Oct
BEGINS
Chicago, Illinois
22
Oct
CONCLUDES
Chicago, Illinois
Duration
6 days
5 nights
What's Included
12 meals ( 5B, 4L, 3D )
3 expert-led lectures
8 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Pay in Full 4,998
OR
Pay Deposit 100
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