Ask people about the tallest buildings in Chicago, and the conversation will turn quickly to architecture. Every new high-rise faces the pressure of fitting into the city’s iconic skyline.

So what did that process look like over time? In what context was each new building judged? We’ve cataloged the fifty tallest buildings in Chicago and plotted them chronologically.

Get a sense of what the skyline looked like as years passed, from a barren beginning in the 1930s to the dense, layered triumphs of modern architecture.

1930s

Building	Height (ft)	Floors	Year	Rank
Chicago Board of Trade Building	605	44	1930	41

1940s

No existing buildings built in the 1940s are among Chicago’s tallest buildings.

1950s

Building	Height (ft)	Floors	Year	Rank
One Prudential Plaza	601	41	1955	42 (tie)

1960s

Building	Height (ft)	Floors	Year	Rank
1000 Lake Shore Plaza	590	55	1964	47
Richard J. Daley Center	648	32	1965	29
Lake Point Tower	645	70	1968	31
John Hancock Center	1,127	100	1969	4
Chase Tower	850	60	1969	11

1970s

Building	Height (ft)	Floors	Year	Rank
CNA Center	601	44	1972	42 (tie)
Mid-Continental Plaza	583	49	1972	50
Aon Center	1,136	83	1973	3
330 North Wabash	695	52	1973	20
Willis Tower	1,450	108	1974	1
Water Tower Place	859	74	1976	9

1980s

Building	Height (ft)	Floors	Year	Rank
Three First National Plaza	767	57	1981	15
Madison Plaza	599	44	1982	45
One Magnificent Mile	673	57	1983	25
Olympia Centre	725	63	1986	19
Citigroup Center	588	42	1987	49
Franklin Center North Tower	1,007	61	1989	5
900 North Michigan	871	66	1989	8
Leo Burnett Building	635	50	1989	35
NBC Tower	627	37	1989	37

1990s

Building	Height (ft)	Floors	Year	Rank
Two Prudential Plaza	995	64	1990	6
311 South Wacker Drive	961	65	1990	7
181 West Madison Street	680	50	1990	23
Chicago Place	608	49	1991	40
Grant Thornton Tower	755	50	1992	16
77 West Wacker Drive	668	49	1992	27
Heller International Building	600	45	1992	44

2000s

Building	Height (ft)	Floors	Year	Rank
Park Tower	844	67	2000	12
One North Wacker	652	50	2001	28
River East Center	644	58	2001	32
55 East Erie Street	647	56	2003	30
Grand Plaza I	641	57	2003	33
Millennium Centre	610	58	2003	39
111 South Wacker Drive	681	51	2005	22
Hyatt Center	679	48	2005	24
The Heritage at Millennium Park	631	57	2005	36
340 on the Park	672	64	2007	26
The Clare	589	52	2008	48
Trump International Hotel and Tower	1,389	98	2009	2
Aqua	859	82	2009	10
300 North LaSalle	784	60	2009	14
One Museum Park	726	62	2009	18
155 North Wacker	638	45	2009	34
353 North Clark	624	44	2009	38

2010s

Building	Height (ft)	Floors	Year	Rank
The Legacy at Millennium Park	822	73	2010	13
Blue Cross Blue Shield Tower	743	57	2010	17
Waldorf Astoria Chicago	686	60	2010	21
The Grant	595	54	2010	46
OneEleven	630	59	2014	36