- Trip 1 - 10 places 3.9 miles in Category:Illinois
- Link to the Trip Map
- Newberry_Plaza - Skyscrapers - 41°54′06″N 87°37′44″W / 41.9016°N 87.6289°W
- Fisher_Studio_Houses - Landmarks - 41°54′15″N 87°37′43″W / 41.9043°N 87.6285°W
- 1000_Lake_Shore_Plaza - Residential_skyscrapers - 41°54′04″N 87°37′28″W / 41.901°N 87.6245°W
- Four_Seasons_Hotel_Chicago - Skyscraper_hotels - 41°53′59″N 87°37′30″W / 41.8997°N 87.625°W
- Plaza_on_DeWitt - Residential_condominiums - 41°53′55″N 87°37′11″W / 41.8986°N 87.6197°W
- 680_N_Lake_Shore_Drive - Office_buildings - 41°53′41″N 87°37′00″W / 41.8946°N 87.6168°W
- MacCormac_College - Universities_and_colleges - 41°52′54″N 87°37′36″W / 41.8818°N 87.6267°W
- Bataan-Corregidor_Memorial_Bridge - Bridges - 41°53′15″N 87°37′41″W / 41.8875°N 87.628°W
- Shivalya_of_Downtown_Chicago - Hindu_temples - 41°53′30″N 87°38′11″W / 41.8918°N 87.6363°W
- Green_Door_Tavern - Drinking_establishments - 41°53′41″N 87°38′15″W / 41.8946°N 87.6374°W
- Trip 2 - 10 places 10.7 miles in Category:Illinois
- Link to the Trip Map
- Adams_Wildlife_Sanctuary - Protected_areas - 39°48′11″N 89°37′08″W / 39.8031°N 89.6189°W
- Midwest_Technical_Institute - For-profit_universities_and_colleges - 39°50′26″N 89°35′40″W / 39.8405°N 89.5944°W
- Lanphier_Park - Baseball_venues - 39°49′02″N 89°38′11″W / 39.8171°N 89.6364°W
- Lanphier_High_School - Schools - 39°49′04″N 89°38′23″W / 39.8178°N 89.6396°W
- Benedictine_University_at_Springfield - Roman_Catholic_universities_and_colleges - 39°49′12″N 89°38′42″W / 39.82°N 89.645°W
- World_War_II_Illinois_Veterans_Memorial - World_War_II_memorials - 39°49′11″N 89°39′41″W / 39.8197°N 89.6615°W
- Illinois_State_Museum - Museums - 39°47′48″N 89°39′19″W / 39.7967°N 89.6554°W
- Leland_Hotel_(Springfield,_Illinois) - Hotels - 39°47′54″N 89°38′53″W / 39.7983°N 89.6481°W
- Hoogland_Center_for_the_Arts - Theatres - 39°47′52″N 89°38′51″W / 39.7977°N 89.6475°W
- Prairie_Capital_Convention_Center - Buildings_and_structures - 39°48′03″N 89°38′40″W / 39.8009°N 89.6444°W
- Trip 3 - 10 places 11.4 miles in Category:Illinois
- Link to the Trip Map
- Glenbard_East_High_School - Schools - 41°51′58″N 88°01′18″W / 41.8662°N 88.0216°W
- National_University_of_Health_Sciences - Universities_and_colleges - 41°51′36″N 88°00′53″W / 41.86°N 88.0146°W
- Helen_M._Plum_Memorial_Library - Public_libraries - 41°53′03″N 88°01′13″W / 41.8841°N 88.0203°W
- Lilacia_Park - Protected_areas - 41°53′07″N 88°01′14″W / 41.8852°N 88.0205°W
- Hadley_Junior_High_School - Public_middle_schools - 41°52′54″N 88°04′50″W / 41.8817°N 88.0806°W
- Marion_E._Wade_Center - Literary_museums - 41°52′14″N 88°06′04″W / 41.8706°N 88.1012°W
- Edman_Memorial_Chapel - Buildings_and_structures - 41°52′12″N 88°06′02″W / 41.8699°N 88.1006°W
- College_Church - Churches - 41°52′04″N 88°06′06″W / 41.8678°N 88.1017°W
- Milton_Township,_DuPage_County,_Illinois - Townships - 41°51′31″N 88°05′22″W / 41.8586°N 88.0894°W
- Flowerfield,_Illinois - Unincorporated_communities - 41°52′02″N 88°02′02″W / 41.8672°N 88.0339°W
- Trip 4 - 10 places 18.0 miles in Category:Illinois
- Link to the Trip Map
- Raupp_Museum - Museums - 42°10′12″N 87°58′42″W / 42.1701°N 87.9782°W
- Vernon_Township,_Lake_County,_Illinois - Townships - 42°11′49″N 87°56′33″W / 42.1969°N 87.9425°W
- Vernon_Area_Public_Library_District - Public_libraries - 42°11′55″N 87°56′11″W / 42.1986°N 87.9364°W
- Marriott_Theatre - Buildings_and_structures - 42°11′38″N 87°55′41″W / 42.194°N 87.928°W
- Lincolnshire_Commons - Shopping_malls - 42°10′57″N 87°55′39″W / 42.1824°N 87.9276°W
- Wheeling_High_School - Public_high_schools - 42°07′34″N 87°56′21″W / 42.1262°N 87.9392°W
- John_Hersey_High_School - Schools - 42°06′14″N 87°57′34″W / 42.1039°N 87.9594°W
- St._Viator_High_School - Private_high_schools - 42°05′39″N 87°58′10″W / 42.0942°N 87.9694°W
- Christian_Liberty_Academy - Christian_schools - 42°05′23″N 87°59′22″W / 42.0897°N 87.9894°W
- Paylocity_Corporation - Business_services_companies - 42°08′45″N 88°00′16″W / 42.1459°N 88.0045°W
- Trip 5 - 10 places 20.4 miles in Category:Illinois
- Link to the Trip Map
- Addison_Street - Streets - 42°02′31″N 88°16′14″W / 42.0419°N 88.2705°W
- Grand_Victoria_Casino_Elgin - Casinos - 42°01′52″N 88°16′49″W / 42.031°N 88.2803°W
- St._Edward_Central_Catholic_High_School_(Elgin,_Illinois) - Schools - 42°01′57″N 88°17′20″W / 42.0325°N 88.2889°W
- South_Elgin,_Illinois - Villages - 41°59′32″N 88°18′28″W / 41.9922°N 88.3078°W
- Elgin_Community_College - Two-year_colleges - 42°01′05″N 88°19′20″W / 42.0181°N 88.3222°W
- Elgin_Township,_Kane_County,_Illinois - Townships - 42°01′33″N 88°19′14″W / 42.0258°N 88.3206°W
- Udina,_Illinois - Populated_places - 42°02′36″N 88°22′34″W / 42.0433°N 88.3761°W
- Advocate_Sherman_Hospital - Hospitals - 42°04′12″N 88°19′49″W / 42.0699°N 88.3302°W
- Spring_Hill_Mall - Shopping_malls - 42°06′10″N 88°17′42″W / 42.1028°N 88.295°W
- The_Einstein_Academy_(Elgin,_Illinois) - Private_high_schools - 42°04′00″N 88°17′54″W / 42.0668°N 88.2982°W
- Trip 6 - 10 places 23.3 miles in Category:Illinois
- Link to the Trip Map
- Savoy,_Illinois - Villages - 40°03′48″N 88°15′09″W / 40.0633°N 88.2525°W
- University_of_Illinois_Institute_of_Aviation - None - 40°02′22″N 88°15′19″W / 40.0394°N 88.2552°W
- Champaign_Township,_Champaign_County,_Illinois - Townships - 40°05′36″N 88°18′28″W / 40.0933°N 88.3078°W
- Judah_Christian_School - Schools - 40°07′29″N 88°18′25″W / 40.1247°N 88.3069°W
- Augerville,_Illinois - Unincorporated_communities - 40°08′23″N 88°10′18″W / 40.1397°N 88.1717°W
- Station_Theatre_(Urbana) - Theatres - 40°06′53″N 88°12′29″W / 40.1148°N 88.2081°W
- Carle_Foundation_Hospital - Hospitals - 40°07′01″N 88°12′54″W / 40.1169°N 88.215°W
- Activities_and_Recreation_Center - Buildings_and_structures - 40°06′05″N 88°14′10″W / 40.1013°N 88.236°W
- Wolfram_Research - Mathematical_software - 40°05′50″N 88°14′45″W / 40.0971°N 88.2457°W
- Illinois_Natural_History_Survey - University_museums - 40°05′34″N 88°14′23″W / 40.0929°N 88.2398°W
- Trip 7 - 10 places 28.2 miles in Category:Illinois
- Link to the Trip Map
- Keeling-Puri_Peace_Plaza - Outdoor_sculptures - 42°18′57″N 88°58′50″W / 42.3157°N 88.9806°W
- Caledonia,_Illinois - Villages - 42°22′04″N 88°53′33″W / 42.3678°N 88.8925°W
- Caledonia_Township,_Boone_County,_Illinois - Townships - 42°22′15″N 88°54′06″W / 42.3708°N 88.9017°W
- Argyle,_Illinois - Unincorporated_communities - 42°22′N 88°56′W / 42.36°N 88.94°W
- Harlem_High_School_(Illinois) - Schools - 42°21′21″N 89°01′32″W / 42.3558°N 89.0256°W
- Machesney_Park_Mall - Buildings_and_structures - 42°21′01″N 89°03′11″W / 42.3504°N 89.053°W
- Frank_E._Bauer_Bridge - Former_toll_bridges - 42°20′18″N 89°03′58″W / 42.3384°N 89.0661°W
- Boylan_Catholic_High_School - High_schools - 42°19′13″N 89°05′00″W / 42.3203°N 89.0833°W
- BMO_Harris_Bank_Center - Basketball_venues - 42°16′13″N 89°05′46″W / 42.2703°N 89.0961°W
- Rockford_East_High_School - Public_high_schools - 42°15′25″N 89°03′00″W / 42.2569°N 89.0501°W
- Trip 8 - 10 places 26.3 miles in Category:Illinois
- Link to the Trip Map
- State_Park_Place,_Illinois - Unincorporated_communities - 38°39′31″N 90°02′50″W / 38.6586°N 90.0472°W
- Caseyville,_Illinois - Villages - 38°37′59″N 90°01′58″W / 38.6331°N 90.0328°W
- Fairview_Heights,_Illinois - Cities - 38°35′38″N 89°59′48″W / 38.5939°N 89.9967°W
- Berean_Christian_School_(Fairview_Heights,_Illinois) - Christian_schools - 38°34′38″N 89°58′57″W / 38.5772°N 89.9825°W
- Birkner,_Illinois - Coal_mining - 38°33′43″N 90°01′44″W / 38.562°N 90.029°W
- National_Shrine_of_Our_Lady_of_the_Snows - Churches - 38°33′40″N 90°05′32″W / 38.5612°N 90.0923°W
- East_St._Louis_Senior_High_School - Public_high_schools - 38°36′31″N 90°06′12″W / 38.6086°N 90.1033°W
- 29th_Street_Yard_(St._Louis_MetroLink) - United_States_light_rails - 38°37′12″N 90°07′04″W / 38.6201°N 90.1179°W
- East_St._Louis_Community_College_Center - Universities_and_colleges - 38°37′15″N 90°09′44″W / 38.6207°N 90.1623°W
- Emerson_Park_station_(MetroLink) - None - 38°37′44″N 90°08′13″W / 38.6288°N 90.1369°W
- Trip 9 - 10 places 30.1 miles in Category:Illinois
- Link to the Trip Map
- Crab_Orchard_and_Egyptian_Railway - Spin-offs - 37°44′02″N 88°55′42″W / 37.734°N 88.9283°W
- Crab_Orchard_National_Wildlife_Refuge - Landforms - 37°42′00″N 89°03′33″W / 37.7°N 89.0592°W
- John_A._Logan_College - Museums - 37°44′52″N 89°05′20″W / 37.7478°N 89.0889°W
- Herrin,_Illinois - Coal_towns - 37°48′09″N 89°01′41″W / 37.8025°N 89.0281°W
- Herrin_Precinct,_Williamson_County,_Illinois - Townships - 37°49′04″N 88°59′03″W / 37.8178°N 88.9842°W
- Johnston_City,_Illinois - Cities - 37°49′15″N 88°55′39″W / 37.8208°N 88.9275°W
- Halfway,_Illinois_(Little_Juarez) - Populated_places - 37°47′34″N 88°56′01″W / 37.7928°N 88.9335°W
- Whiteash,_Illinois - Villages - 37°47′18″N 88°55′35″W / 37.7883°N 88.9264°W
- Dog_Walk,_Illinois - Unincorporated_communities - 37°45′33″N 88°55′58″W / 37.7592°N 88.9328°W
- Rent_One_Park - Buildings_and_structures - 37°44′46″N 88°57′37″W / 37.746°N 88.9604°W
- Trip 10 - 10 places 32.5 miles in Category:Illinois
- Link to the Trip Map
- Goodenow_Grove_Nature_Preserve - Nature_centers - 41°24′14″N 87°36′07″W / 41.404°N 87.602°W
- Sauk_Lake - Lakes - 41°29′16″N 87°39′18″W / 41.4877°N 87.6551°W
- Prairie_State_College - Universities_and_colleges - 41°31′41″N 87°38′17″W / 41.528°N 87.638°W
- Flossmoor,_Illinois - Villages - 41°32′30″N 87°41′06″W / 41.5417°N 87.685°W
- Country_Club_Hills,_Illinois - Cities - 41°33′44″N 87°43′15″W / 41.5622°N 87.7208°W
- Hollywood_Casino_Amphitheatre_(Tinley_Park,_Illinois) - Music_venues - 41°32′38″N 87°46′34″W / 41.544°N 87.776°W
- Rich_Township,_Cook_County,_Illinois - Townships - 41°30′45″N 87°43′56″W / 41.5125°N 87.7322°W
- Rich_East_High_School - Public_high_schools - 41°28′51″N 87°41′26″W / 41.4809°N 87.6905°W
- Thorn_Creek_Nature_Center_and_Preserve - Buildings_and_structures - 41°28′N 87°41′W / 41.46°N 87.69°W
- Goodenow,_Illinois - Unincorporated_communities - 41°23′29″N 87°38′12″W / 41.3914°N 87.6367°W