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Chicago Highlights: My Kind of Town

Chicago; Photo Credit Songquan Deng
Chicago Navy Pier; Photo Credit Kenn W. Kiser Lake Michigan Boat Cruise; Photo Credit Yvonne Stepanow Chicago's Sears Tower; Photo Credit Matt Thompson Chicago; Photo Credit Songquan Deng

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Mon – Fri, 8:30 AM to 5:00 PM EST

The "Windy City" is just bursting with breathtaking architecture, wonderful museums, fantastic restaurants, a beautiful lakefront, and world-class shopping.


7 Days/6 Nights

Meals Included:

2 Breakfasts, 2 Dinners


$1,149.95 Per Person

NOTE: Itinerary subject to change

Day 1:
Travel to Independence, OH
Lunch on own
One overnight at Doubletree Hotel
Dinner on own

Day 2:
Breakfast at hotel
Check out and travel to Cleveland, OH
Admission to the Rock n' Roll Hall of Fame
Lunch on own at the Hall of Fame
Travel to Chicago, IL
(Time change one hour behind to Central Time)
Four overnights at the Holiday Inn Chicago Mart Plaza
Dinner on own

Day 3:
Breakfast on own
Travel to Glencoe, IL
Admission and Tram tour through the Chicago Botanic Gardens
Lunch on own at the Gardens
Return to Chicago
Narrated Chicago Trolley Tour
Dinner and evening on own at Navy Pier

Day 4:
Breakfast on own
Admission to the Field Museum of Natural History and one special exhibit
Lunch on own
Remainder of day on own to explore Chicago
Dinner on own

Day 5:
Breakfast on own
Skydeck Chicago
Free Time and lunch on own at the Magnificent Mile
Boat Cruise of Lake Michigan and the Chicago River
Return to hotel
Dinner and show at Tommy Gun's Garage

Day 6:
Breakfast on own
Check out and travel to Pittsburgh, PA
Lunch on own
(Time change one hour ahead to Eastern Standard Time)
One overnight at Double Tree Pittsburgh/Greentree
Dinner at Grand Concourse Restaurant in Station Square

Day 7:
Breakfast at hotel
Check out
Admission and guided tour of the Nationality Rooms
Lunch on own
Travel home

Every Starr trip includes deluxe motorcoach transportation and overnight accommodations.
Rock 'n Roll Hall of Fame
The World's only facility dedicated to the living heritage of rock and roll music. Designed by I.M. Pei, the $92 million structure towers above Lake Erie's shore at North Coast Harbor. The new Hall of Fame wows visitors with high-impact, multi-media production combining film footage, music, interviews, animation and still photography to tell the stories of inducted rock and roll legends.

Chicago Botanic Gardens Grand Tram Tour
The 385-acre Garden features 23 display gardens and three native habitats, uniquely situated on nine islands surrounded by lakes. Enjoy a fact-filled, 45-minute narrated tour providing an overview of the garden's 385 acres. Tram includes views of the Japanese Garden, 100-acre oak woodland, and the native prairie.

Trams are wheelchair-accessible.

Chicago Trolley Tour
Two hour narrated tour of Downtown Chicago on an authentic trolley with professional tour personnel to tell you truth and a little fiction about the city called "windy." Hear the history of the city and see the sights for which it's famous including Grant Park, fabulous architecture, outdoor art, and much more.

Navy Pier
Navy Pier has been a treasured Chicago landmark since its construction in 1916. It boasts dozens of restaurants and shops, special exhibits, entertainment, and gardens. Activities can include a ride on the incredible fifteen story Ferris Wheel, giving one of the best views of the Chicago Skyline and the turn of the century style carousel which features 36 hand painted animals.

Field Museum of Natural History
One of America's premier natural history museums, the Field's "Live over Time" exhibit houses "Sue," the largest and most complete Tyrannosaurus rex ever discovered. The Field Museum boasts a number of both permanent and temporary exhibits that will appeal to museum goers of all ages.

All Access Pass includes all permanent and special exhibitions and 3D movie.

Wheelchairs are available on a first-come, first-served basis free of charge at the East Entrance & the Coat Check.

Lake Michigan and Chicago River Boat Cruise
Chicago's most comprehensive boat tour. This signature tour of Lake Michigan and the Chicago River includes a trip through the Chicago Lock and a live narration featuring an overview of architecture and history.

Boat is wheelchair accessible.

NOTE: Passengers must navigate steps to get to the actual dock. Persons with walking disabilities may find this difficult.

Vessels include open air and covered seating, men's and woman's restrooms, and a snack bar & cash bar.

Magnificent Mile
Take a magnificent vacation in just eight spectacular blocks. Explore over 400 exclusive stores and boutiques, enjoy fine dining at over 200 restaurants, marvel at Chicago's famous architecture and learn first hand why North Michigan Avenue is called The Magnificent Mile.

Skydeck Chicago
Skydeck Chicago offers an unsurpassed view of Chicago and 4 surrounding states. Take an elevator to the 103rd floor and see the breathtaking panorama.

"The Ledge" dares visitors to attempt a unique Chicago experience: stand on The Ledge and feel the city from 103 floors over Wacker Drive and the Chicago River.

Admission also includes interactive exhibits and signature photo opportunities.

Tommy Gun's Garage Restaurant
First, enjoy dinner served by da gangsters and flappers who are also the actors and actresses. After dinner, da show begins. Tommy Gun's Garage is an audience interactive musical comedy revue wit gangsters, flappers and YOU! "Vito," "Gloves," da "Mugs," and da "Moll" will entertain yous guys wit non-stop comedy and dangerous fun. Hide your hooch because the joint even gets raided by da cops complete with a sobriety test. You will have a Roaring Time in the Twenties Tradition.

Nationality Rooms
The Nationality Rooms are a collection of 27 classrooms in the University of Pittsburgh's Cathedral of Learning depicting and donated by the ethnic groups that helped build the city of Pittsburgh. The rooms are designated as a Pittsburgh History and Landmarks Foundation historical landmark and are located on the 1st and 3rd floors of the Cathedral of Learning, itself a national historic landmark, on the University of Pittsburgh's main campus.

Although of museum caliber, twenty-five of the 27 rooms are in almost constant use as functional classrooms and utilized daily by University of Pittsburgh faculty and students, while the other two are display rooms which can be explored only via guided tour.

Accomodations Day 1: Doubletree Hotel, Independence, OH

The Doubletree Cleveland South hotel offers Doubletree's world famous "Sweet Dreams" Bedding which includes a pillow top mattress, down comforter and down pillows. All guestrooms offer complimentary internet access and those famous Doubletree chocolate chip cookies at check in.

The hotel also offers a full-service restaurant and bar, 24-hour fitness center, and indoor/outdoor pool.

Shulas2 Steakhouse, a premier sports restaurant, features athlete-sized appetizers, incredible steaks featuring the exclusive Shula's Cut, a fun kid's menu, 37 big-screen TVs and sports memorabilia. Serves breakfast, lunch, and dinner.

Cots are $15 per night and refrigerators are $15 per stay.

Accommodations Day 2, 3, 4 & 5: Holiday Inn Chicago Mart Plaza, Chicago, IL

The Holiday Inn Chicago Mart Plaza is located adjacent to the Chicago Merchandise Mart and has the best views of all Downtown Chicago, seen from the top of the Chicago Apparel Center.

The hotel features an indoor pool and fitness canter.

You will eat well when you're a guest at Chicago Mart Plaza. Serving seasonal, "elevated" comfort food atop Wolf Point, Merchants Cafe offers a new take on American cuisine. Chow down on hearty dishes to warm your belly, or enjoy fresh, lighter fare for dinner or a late night dinner. Breakfast features a tempting buffet while dinner centers on individual flatbreads, salads, sizzling ribs, classic burgers, and fresh fish.
Visit Merchants Market for hot and cold signature sandwiches, salads, coffee, beer, and wine. The CityScape Bar offers light fare and specialty cocktails.

Guestrooms include coffee maker, iron/board, hairdryer, and complimentary WIFI.

The Holiday Inn Chicago Mart Plaza is within walking distance to great restaurants, intimate wine bars, exotic art galleries, stunning architecture, and a wealth of other cultural attractions.

Rollaway beds: $20 per night plus tax. Cannot have a cot in double bedded rooms. Subject to change.

Accommodations Day 6: Doubletree Pittsburgh/Greentree

Experience the DoubleTree by Hilton Hotel Pittsburgh - Green Tree. Set on the south side and only 3 miles from downtown, this hotel features indoor/outdoor pool and fitness center.

Visit Seasons Restaurant for breakfast, lunch or dinner and enjoy American dinner classics executed with local flair. Unwind with a cocktail at Champions Lounge or grab a bite and catch-up on entertainment and sports. The Marketplace Bistro offers a casual dining experience.

Guest rooms are well appointed and include a Sweet Dreams by Doubletree bed, cable television with premium channels, wireless internet, hair dryer, iron and ironing board, and coffee maker.

-Please note Chicago is a large metropolitan city and walking more than 2-3 blocks at a time will be required on this trip.

-Please note Chicago is a large metropolitan city and walking more than 2-3 blocks at a time will be required on this trip.

Boat Tour NOTE: Boat is wheelchair accessible; however you must go down approximately 60 (easy) steps to get to the actual dock. Persons with walking disabilities may find this difficult.

Starr has a select quantity of wheelchair accessible motorcoaches available; therefore, we suggest you contact a Travel Advisor to discuss any needs you may have before reserving your trip.

Important Tour Policies – Please review these important Starr policies prior to booking your trip:

Tour Protection   |   Cancellation Policy   |   General Tour Information