Close Icon
Gear IconImportant Reminder:The City Guide app will be sunsetting on December 15, 2024, with the web version to follow in early 2025. Please visit our FAQ to learn more or to download our Swarm app.
Learn more
Chicago Roadtrip
Fairfield Inn & Suites Seymour is one of Chicago Roadtrip.

1. Fairfield Inn & Suites Seymour

5.6
327 North Sandy Creek Drive, Seymour, IN
Hotel · 7 tips and reviews
Steak 'n Shake is one of Chicago Roadtrip.

2. Steak 'n Shake

5.3
1236 W. S.R. 32 (at Garoffolo Blvd), Lebanon, IN
American Restaurant · 19 tips and reviews
Meadow Lake Wind Farm is one of Chicago Roadtrip.

3. Meadow Lake Wind Farm

5.7
White County (along Interstate 65), Brookston, IN
Farm · 78 tips and reviews
Chili's Grill & Bar is one of Chicago Roadtrip.

4. Chili's Grill & Bar

6.6
7140 Mannheim Rd, Rosemont, IL
Tex-Mex Restaurant · 37 tips and reviews

5. Intersection: Oakton and Lee St.

(Oakton Street), Des Plaines, IL
Road · No tips or reviews
Kmart is one of Chicago Roadtrip.

6. Kmart

1155 E Oakton St (at Lee St), Des Plaines, IL
Department Store · 8 tips and reviews
Starbucks is one of Chicago Roadtrip.

7. Starbucks

7.3
7000 Mannheim Rd (at Target), Rosemont, IL
Coffee Shop · No tips or reviews
Target is one of Chicago Roadtrip.

8. Target

7.6
7000 Mannheim Rd (at Lunt St), Rosemont, IL
Big Box Store · 20 tips and reviews
Holiday Inn and Suites Chicago O'Hare Rosemont Hotel is one of Chicago Roadtrip.

9. Holiday Inn and Suites Chicago O'Hare Rosemont Hotel

10233 W Higgins Rd, Rosemont, IL
Hotel · 25 tips and reviews
Village of Rosemont is one of Chicago Roadtrip.

10. Village of Rosemont

Rosemont, IL
Village · 5 tips and reviews
Toll Plaza 17 is one of Chicago Roadtrip.

11. Toll Plaza 17

Devon Avenue (I-90), Rosemont, IL
Toll Plaza · 12 tips and reviews
Harry Caray's cow statue is one of Chicago Roadtrip.

12. Harry Caray's cow statue

Des Plaines, IL
Sculpture Garden · No tips or reviews
The Magnificent Mile is one of Chicago Roadtrip.

13. The Magnificent Mile

N Michigan Ave (btwn E Oak St & Chicago River), Chicago, IL
Road · Streeterville · 90 tips and reviews
DuSable Bridge is one of Chicago Roadtrip.

14. DuSable Bridge

350 N Michigan Ave (at E Wacker Dr), Chicago, IL
Bridge · The Loop · 41 tips and reviews
Sheraton Grand Chicago Riverwalk is one of Chicago Roadtrip.

15. Sheraton Grand Chicago Riverwalk

7.9
301 E North Water St (at N Columbus Dr), Chicago, IL
Hotel · Streeterville · 133 tips and reviews
McCormick & Schmick's is one of Chicago Roadtrip.

16. McCormick & Schmick's

4999 Old Orchard Ctr., North Ring Rd. (at Skokie Blvd.), Skokie, IL
Seafood Restaurant · 28 tips and reviews
Bloomingdale's is one of Chicago Roadtrip.

17. Bloomingdale's

6.9
4963 Old Orchard Ctr, Skokie, IL
Department Store · 5 tips and reviews
Nordstrom is one of Chicago Roadtrip.

18. Nordstrom

8.8
4937 Old Orchard Ctr, Skokie, IL
Women's Store · 23 tips and reviews
Banana Republic is one of Chicago Roadtrip.

19. Banana Republic

7.7
4999 Old Orchard Ctr Ste L14, Skokie, IL
Clothing Store · 7 tips and reviews
Westfield Old Orchard is one of Chicago Roadtrip.

20. Westfield Old Orchard

8.6
4905 Old Orchard Ctr (btwn Skokie Blvd & Golf Rd), Skokie, IL
Shopping Mall · 47 tips and reviews
Starbucks is one of Chicago Roadtrip.

21. Starbucks

7.1
505 N Michigan Ave (at Illinois St), Chicago, IL
Coffee Shop · Streeterville · 57 tips and reviews
American Girl Place is one of Chicago Roadtrip.

22. American Girl Place

7.0
835 N Michigan Ave (at Water Tower Pl.), Chicago, IL
Toy Store · Streeterville · 52 tips and reviews
Macy's is one of Chicago Roadtrip.

23. Macy's

835 N Michigan Ave Ste 100, Chicago, IL
Department Store · Streeterville · 45 tips and reviews
Pandora is one of Chicago Roadtrip.

24. Pandora

7.4
806 N Michigan Ave (at Water Tower Place), Chicago, IL
Jewelry Store · Streeterville · 3 tips and reviews
Foodlife is one of Chicago Roadtrip.

25. Foodlife

835 N Michigan Ave (at Water Tower Place), Chicago, IL
Food Court · Streeterville · 96 tips and reviews
Columbus Dr Bridge is one of Chicago Roadtrip.

26. Columbus Dr Bridge

Columbus (Wacker), Chicago, IL
Bridge · Streeterville · No tips or reviews
Shula's Steak House is one of Chicago Roadtrip.

27. Shula's Steak House

6.7
301 E North Water St (at N Fairbanks Ct), Chicago, IL
Steakhouse · Streeterville · 14 tips and reviews
Downtown Chicago is one of Chicago Roadtrip.

28. Downtown Chicago

Chicago, IL
Neighborhood · 38 tips and reviews
LaSalle Street Bridge is one of Chicago Roadtrip.

29. LaSalle Street Bridge

N LaSalle St (at W Wacker Dr), Chicago, IL
Bridge · River North · 5 tips and reviews
Clark Street Bridge is one of Chicago Roadtrip.

30. Clark Street Bridge

320 N Clark St (btwn W Kinzie St and W Wacker Dr), Chicago, IL
Bridge · The Loop · 5 tips and reviews
Fulton's on the River is one of Chicago Roadtrip.

31. Fulton's on the River

315 N La Salle Dr (btwn W Kinzie St & N Wacker Dr), Chicago, IL
Seafood Restaurant · River North · 20 tips and reviews
Starbucks is one of Chicago Roadtrip.

32. Starbucks

7.6
444 N Michigan Ave, Chicago, IL
Coffee Shop · Streeterville · 51 tips and reviews
Art Institute of Chicago Museum Shop is one of Chicago Roadtrip.

33. Art Institute of Chicago Museum Shop

8.8
111 S Michigan Ave, Chicago, IL
Gift Store · Grant Park · 20 tips and reviews
The Modern Wing is one of Chicago Roadtrip.

34. The Modern Wing

8.4
159 E. Monroe, Chicago, IL
Art Gallery · Grant Park · 24 tips and reviews
The Art Institute of Chicago is one of Chicago Roadtrip.

35. The Art Institute of Chicago

9.5
111 S Michigan Ave (btwn Monroe St & Jackson Dr), Chicago, IL
Art Museum · Grant Park · 686 tips and reviews
The Rolling Bean is one of Chicago Roadtrip.

36. The Rolling Bean

Chicago, IL
Food Truck · Grant Park · 2 tips and reviews

37. Millennium Park Chiropractic

155 N Michigan Ave (Randolph and Michigan), Chicago, IL
Chiropractor · The Loop · No tips or reviews
Flat Top Grill is one of Chicago Roadtrip.

38. Flat Top Grill

8.3
30 S Wabash Ave (at E Monroe St), Chicago, IL
Vegan and Vegetarian Restaurant · The Loop · 113 tips and reviews
Illinois Center is one of Chicago Roadtrip.

39. Illinois Center

111 E Wacker (btwn N Michigan Ave and N Stetson Ave), Chicago, IL
Structure · The Loop · 12 tips and reviews
J.Crew is one of Chicago Roadtrip.

40. J.Crew

7.3
900 N Michigan Ave, Chicago, IL
Clothing Store · Streeterville · 9 tips and reviews
900 North Michigan Shops is one of Chicago Roadtrip.

41. 900 North Michigan Shops

7.7
900 N Michigan Ave, Chicago, IL
Shopping Mall · Streeterville · 42 tips and reviews
Sheraton Link Cafe is one of Chicago Roadtrip.

42. Sheraton Link Cafe

5.8
301 E North Water St, Chicago, IL
Café · Streeterville · 1 tip
The Shops At North Bridge is one of Chicago Roadtrip.

43. The Shops At North Bridge

8.1
520 N Michigan Ave (at Grand Ave.), Chicago, IL
Shopping Mall · Streeterville · 23 tips and reviews
Weber Grill Restaurant is one of Chicago Roadtrip.

44. Weber Grill Restaurant

7.9
539 N State St (at Grand Ave), Chicago, IL
American Restaurant · Near North Side · 184 tips and reviews
Tiffany & Co. is one of Chicago Roadtrip.

45. Tiffany & Co.

8.8
730 N Michigan Ave (at E Superior St), Chicago, IL
Jewelry Store · Streeterville · 17 tips and reviews
McCormick Place is one of Chicago Roadtrip.

46. McCormick Place

2301 S Lake Shore Dr (btwn Burnham Harbor Dr. & Access Rd.), Chicago, IL
Convention Center · South Loop · 89 tips and reviews
Mity Nice is one of Chicago Roadtrip.

47. Mity Nice

835 N Michigan Ave, Chicago, IL
American Restaurant · Streeterville · 39 tips and reviews
Banana Republic is one of Chicago Roadtrip.

48. Banana Republic

835 N Michigan Ave, Chicago, IL
Clothing Store · Streeterville · 2 tips and reviews
Water Tower Place is one of Chicago Roadtrip.

49. Water Tower Place

8.1
835 N Michigan Ave (E Pearson St), Chicago, IL
Shopping Mall · Streeterville · 158 tips and reviews
Starbucks is one of Chicago Roadtrip.

50. Starbucks

5.4
2301 S Martin Luther King Dr, Chicago, IL
Coffee Shop · South Loop · 16 tips and reviews
875 North Michigan Avenue is one of Chicago Roadtrip.

51. 875 North Michigan Avenue

875 N Michigan Ave (btwn Delaware Pl & Chestnut St), Chicago, IL
Structure · Streeterville · 206 tips and reviews
The Cheesecake Factory is one of Chicago Roadtrip.

52. The Cheesecake Factory

7.9
875 N Michigan Ave Ste 102, Chicago, IL
American Restaurant · Streeterville · 199 tips and reviews
Chicago Skyway is one of Chicago Roadtrip.

53. Chicago Skyway

I-90 (btwn Dan Ran Expy & Indiana E-W Toll Rd), Chicago, IL
Bridge · East Side · 80 tips and reviews
Indiana Skyway Industrial Wasteland is one of Chicago Roadtrip.

54. Indiana Skyway Industrial Wasteland

6.5
Whiting, IN
Other Great Outdoors · 2 tips and reviews

55. US 31 and CR550N

Columbus, IN
Intersection · No tips or reviews
Exit 80 is one of Chicago Roadtrip.

56. Exit 80

Edinburgh, IN
Road · No tips or reviews
Town of Edinburgh is one of Chicago Roadtrip.

57. Town of Edinburgh

Edinburgh, IN
Town · 2 tips and reviews
Traffic! is one of Chicago Roadtrip.

58. Traffic!

I-65, Edinburgh, IN
Travel and Transportation · No tips or reviews
I-65 & E 500 N is one of Chicago Roadtrip.

59. I-65 & E 500 N

I-65 (E 500 N), Whiteland, IN
Intersection · 4 tips and reviews
South Lake is one of Chicago Roadtrip.

60. South Lake

Greenwood, IN
Housing Development · No tips or reviews
Lucas Oil Stadium is one of Chicago Roadtrip.

61. Lucas Oil Stadium

9.1
500 S Capitol Ave (at W Henry St), Indianapolis, IN
Football Stadium · Downtown Indianapolis · 244 tips and reviews

62. parking

Indianapolis, IN
Parking · Downtown Indianapolis · No tips or reviews
I-65 & IN-47 is one of Chicago Roadtrip.

63. I-65 & IN-47

I-65 (IN-47), Lebanon, IN
Intersection · 1 tip

64. Community of Egypt

Egypt, IN
Village · 1 tip

65. BP

6.0
2636 E Tipton St, Seymour, IN
Fuel Station · No tips or reviews
SUBWAY is one of Chicago Roadtrip.

66. SUBWAY

6.2
1600 E Tipton St, Seymour, IN
Sandwich Spot · No tips or reviews
Walmart Supercenter is one of Chicago Roadtrip.

67. Walmart Supercenter

5.2
1600 E Tipton St, Seymour, IN
Big Box Store · 9 tips and reviews
Henryville Rest Area Southbound is one of Chicago Roadtrip.

68. Henryville Rest Area Southbound

5.9
Interstate 65 Southbound (near Mile Marker 22), Henryville, IN
Rest Area · 24 tips and reviews
Clark Memorial Bridge is one of Chicago Roadtrip.

69. Clark Memorial Bridge

Louisville, KY
Bridge · 6 tips and reviews

70. Bullitt County

Kentucky
County · 1 tip
Kentucky Welcome Center / Rest Area is one of Chicago Roadtrip.

71. Kentucky Welcome Center / Rest Area

7.5
I-65 Southbound (at MM 113.5), Shepherdsville, KY
Rest Area · 23 tips and reviews
Lebanon Junction, KY is one of Chicago Roadtrip.

72. Lebanon Junction, KY

Kentucky
City · 1 tip
Cocoa Bean is one of Chicago Roadtrip.

73. Cocoa Bean

5.5
2800 Opryland Dr (Gaylord Opryland Resort), Nashville, TN
Coffee Shop · 4 tips and reviews
Gaylord Opryland Resort & Convention Center is one of Chicago Roadtrip.

74. Gaylord Opryland Resort & Convention Center

8.5
2800 Opryland Dr, Nashville, TN
Resort · 246 tips and reviews
Cascades American Cafe is one of Chicago Roadtrip.

75. Cascades American Cafe

7.2
2800 Opryland Dr (Gaylord Opryland Resort), Nashville, TN
American Restaurant · 24 tips and reviews
Gaylord Opryland Resort Cascades Waterfall is one of Chicago Roadtrip.

76. Gaylord Opryland Resort Cascades Waterfall

8.8
2800 Opryland Dr, Nashville, TN
Resort · 18 tips and reviews
COACH Outlet is one of Chicago Roadtrip.

77. COACH Outlet

8.2
236 Opry Mills Dr Spc 634A, Nashville, TN
Fashion Accessories Store · 4 tips and reviews
Polo Ralph Lauren Factory Store is one of Chicago Roadtrip.

78. Polo Ralph Lauren Factory Store

7.7
261 Opry Mills Dr, Nashville, TN
Clothing Store · No tips or reviews
Bravo Gelato is one of Chicago Roadtrip.

79. Bravo Gelato

7.1
2800 Opryland Dr (Gaylord Opryland), Nashville, TN
Ice Cream Parlor · 7 tips and reviews
Opry Mills is one of Chicago Roadtrip.

80. Opry Mills

8.7
433 Opry Mills Dr (at Briley Pkwy), Nashville, TN
Shopping Mall · 84 tips and reviews
Opry mills Parking is one of Chicago Roadtrip.

81. Opry mills Parking

Nashville, TN
Parking · 4 tips and reviews
Claim Jumper is one of Chicago Roadtrip.

82. Claim Jumper

514 Opry Mills Drive (Opry Mills Mall), Nashville, TN
American Restaurant · 54 tips and reviews
Canal E is one of Chicago Roadtrip.

83. Canal E

Nashville, TN
Convention Center · 3 tips and reviews
McDonald's is one of Chicago Roadtrip.

84. McDonald's

5.4
1005 E Christi Dr, Dickson, TN
Fast Food Restaurant · 8 tips and reviews
I-40 & TN-46 is one of Chicago Roadtrip.

85. I-40 & TN-46

I-40 (TN-46), Dickson, TN
Intersection · No tips or reviews
Exxon is one of Chicago Roadtrip.

86. Exxon

6.0
2332 Highway 46 S, Dickson, TN
Fuel Station · No tips or reviews
Dickson, TN is one of Chicago Roadtrip.

87. Dickson, TN

Tennessee
City · 3 tips and reviews
Jimmy Evans Memorial Bridge is one of Chicago Roadtrip.

88. Jimmy Evans Memorial Bridge

Interstate 40, Waverly, TN
Bridge · 9 tips and reviews

89. eagle creek bridge

1 (Birdsong Road), Holladay, TN
Bridge · No tips or reviews
Rest Area — I-40 EB is one of Chicago Roadtrip.

90. Rest Area — I-40 EB

6.7
Interstate 40 EB, Holladay, TN
Rest Area · 3 tips and reviews
Rest Area — I-40 WB is one of Chicago Roadtrip.

91. Rest Area — I-40 WB

7.0
I-40 WB (MM 130), Holladay, TN
Rest Area · 8 tips and reviews
Field Of Cotton is one of Chicago Roadtrip.

92. Field Of Cotton

Jackson, TN
Field · No tips or reviews
I-40 & US-70 / US-412 is one of Chicago Roadtrip.

93. I-40 & US-70 / US-412

I-40 (US-70), Jackson, TN
Intersection · 1 tip
I-40 & TN-223 is one of Chicago Roadtrip.

94. I-40 & TN-223

I-40 (TN-223), Jackson, TN
Intersection · 1 tip
Mississippi / Tennessee State Line is one of Chicago Roadtrip.

95. Mississippi / Tennessee State Line

Interstate 55, Southaven, MS
Border Crossing · 6 tips and reviews
City of Southaven is one of Chicago Roadtrip.

96. City of Southaven

Mississippi
City · 4 tips and reviews
I-55 & Nesbit Rd / Pleasant Hill Rd is one of Chicago Roadtrip.

97. I-55 & Nesbit Rd / Pleasant Hill Rd

I-55 (Nesbit Rd), Nesbit, MS
Intersection · 1 tip

98. Green T Lake Lake

Green T Lake, Hernando, MS
Lake · No tips or reviews
Mississippi is one of Chicago Roadtrip.

99. Mississippi

State · 21 tips and reviews
55 South is one of Chicago Roadtrip.

100. 55 South

Winona, MS
Road · No tips or reviews

101. Beside an 18 Wheeler On I 55

Mississippi
Travel and Transportation · No tips or reviews
Kangaroo Express is one of Chicago Roadtrip.

102. Kangaroo Express

100 Colony Crossing Way (Hwy 463), Madison, MS
Fuel Station · 1 tip

103. Exxon

6.1
974 Highway 51 (Madison Ave), Madison, MS
Fuel Station · 2 tips and reviews
Cracker Barrel is one of Chicago Roadtrip.

104. Cracker Barrel

7.5
225 Lakewood Dr, Batesville, MS
American Restaurant · 9 tips and reviews
Cups An Espresso Cafe' is one of Chicago Roadtrip.

105. Cups An Espresso Cafe'

8.5
1903 Main St (Hwy. 463), Madison, MS
Coffee Shop · 12 tips and reviews

106. Woodrow Wilson Bridge

Jackson, Mississippi, Jackson, MS
Bridge · No tips or reviews
Pearl Street Bridge is one of Chicago Roadtrip.

107. Pearl Street Bridge

Jackson, MS
Bridge · 1 tip
Manheim Louisville is one of Chicago Roadtrip.

108. Manheim Louisville

5425 Highway 31 E, Clarksville, IN
Car Dealership · No tips or reviews
Veterans Parkway is one of Chicago Roadtrip.

109. Veterans Parkway

Clarksville, IN
Road · No tips or reviews
Interstate 65 is one of Chicago Roadtrip.

110. Interstate 65

Interstate 65 (btwn I-64 & KY-44), Louisville, KY
Road · 3 tips and reviews
Jefferson Mall is one of Chicago Roadtrip.

111. Jefferson Mall

5.7
4801 Outer Loop (Jefferson Blvd), Louisville, KY
Shopping Mall · Okolona · 28 tips and reviews
City of Bowling Green is one of Chicago Roadtrip.

112. City of Bowling Green

Kentucky
City · 20 tips and reviews
Kentucky / Tennessee State Line is one of Chicago Roadtrip.

113. Kentucky / Tennessee State Line

I-65 (btwn TN 52 & US 31W), Portland, TN
Border Crossing · 24 tips and reviews
Exxon is one of Chicago Roadtrip.

114. Exxon

4763 Scottsville Rd, Bowling Green, KY
Fuel Station · 1 tip
Cracker Barrel is one of Chicago Roadtrip.

115. Cracker Barrel

8.3
1960 Mel Browning St, Bowling Green, KY
American Restaurant · 24 tips and reviews
Water's Edge at Delta Island Opryland is one of Chicago Roadtrip.

116. Water's Edge at Delta Island Opryland

Nashville, TN
Hotel · 2 tips and reviews
Aquarium Restaurant is one of Chicago Roadtrip.

117. Aquarium Restaurant

7.5
516 Opry Mills Dr (at McGavock Pk), Nashville, TN
Seafood Restaurant · 60 tips and reviews
I-65 & US-31 is one of Chicago Roadtrip.

118. I-65 & US-31

I-65 (US-31), Falkville, AL
Intersection · 1 tip
Smoke Rise, AL is one of Chicago Roadtrip.

119. Smoke Rise, AL

Warrior, AL
Home (private) · 6 tips and reviews

120. Mini Grand Canyon

Alabama
Hiking Trail · No tips or reviews
Panera Bread is one of Chicago Roadtrip.

121. Panera Bread

8.2
1800 McFarland Blvd E Ste 402, Tuscaloosa, AL
Bakery · 32 tips and reviews
Midtown Village is one of Chicago Roadtrip.

122. Midtown Village

8.3
1800 McFarland Blvd E, Tuscaloosa, AL
Shopping Plaza · 26 tips and reviews

123. Highway 98

(I-59), Hattiesburg, MS
Bridge · No tips or reviews