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48 hours in Chicago - see the best of the Midwest in a weekend

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Perched on the edge of enormous Lake Michigan, Chicago’s size and famous skyline mark it out as the undisputed “King of the Midwest”. The Windy City is full of iconic sights and its closely-packed and distinct neighborhoods mean a visitor can see a huge amount in a weekend. Here is our recommended itinerary for getting the full Chicago experience in 48 hours.


5 p.m. - Once you touch down, your first job will be to get into downtown Chicago. Both O’Hare and Midway airports are close enough to get a taxi, but taking the CTA train will almost always be a cheaper and faster option – especially during rush hour. Make sure to check with your hotel too, as many offer complimentary shuttle vans from the airport.

7 p.m. - When you’ve checked in, take in your first views of the city from the window of the L train as you rattle up the tracks to the North Side. There you can relax in the delightful open spaces of Lincoln Park. Just to the north of the park is Wrigley Field, home of the Chicago Cubs. The oldest ballpark in America, to enter its historic ivy-covered walls is to be transported back to early 20th century and this American icon is a must-see even when there isn’t a game on.


9 p.m. - A few minutes’ walk south of Wrigley Field is Giordano’s, the place to go to get a typical Chicago deep-dish pizza, filled with thick sticky cheese and rich tomato sauce. Another of Chi-Town’s most celebrated exports is house music, and if you want to dance the night away, grab a cab a few blocks to Smart Bar for a good time until the early hours. If you’re in the mood for a quieter night, the two-screen Music Box Theatre is just as close and shows cult hits and art-house fare.



9 a.m. - Start your first full day in Chicago with an early visit to its most distinctive monument – the colossal Sears Tower, now officially the Willis Tower, although you won’t find many native Chicagoans who call it that. The building’s “Skydeck” offers amazing views over the city, and if you’re feeling brave there are glass-bottomed “skyboxes” that stick out from the edge of the structure.


11 a.m. - Once you’ve descended, a lavish brunch at the Frontera Grill is just a short cab ride away. The Rick Bayless-owned restaurant specializes in eggs – try the spicy Bajio-style, served in crispy tortilla boats.


12 p.m. - Next head down the road for a wander in Grant Park, which lies on the shoreline right in the heart of the city. Within the park’s boundary is the Art Institute of Chicago, where you can experience some distinctively American artwork, from Grant Wood’s American Gothic to Edward Hopper’s Nighthawks. If that’s not your thing, the fascinating Chicago Cultural Center is just across the road.


2 p.m. - You can’t leave Chicago without trying another local specialty – the hot dog. Drop in to hipster hole-in-the-wall Max’s Take Out and get one to go, but remember: don’t ask for ketchup! That’s a serious faux-pas in the Windy City.


5 p.m. - Juicy dog in hand, head north over the Chicago River onto the Magnificent Mile, the downtown strip where Mr. Selfridge learned his trade. You’ll spot plenty of memorable landmarks as your make your way north, including the Allerton Hotel, Tribune Tower and the Wrigley Building.


6 p.m. - At the far end of the “Mag Mile” is the Chicago Water Tower, a rare remnant of Chicago before the great fire, and now home of little known gem, the City Gallery.



9 a.m. - With north and downtown Chicago covered, your last day is your chance to head to the south side of town. Start with an early morning wander along the Lakefront Trail through Jackson Park, making sure to check out the peaceful Osaka Gardens, which lie on a wooded isle hidden between sleepy lagoons.


11 a.m. - Just beyond the gardens you’ll find the Museum of Science and Industry. The largest science museum in the Western Hemisphere, it is famous amongst the schoolchildren of Illinois as being the best school trip around. Housed in the elegant former Palace of Fine Arts and full of interactive exhibits, it’s an unmissable experience featuring a full size replica coal mine and a captured Nazi submarine.


2 p.m. - Once you can drag yourself away from the MSI, head north out of the park for a foaming beer at The Cove Lounge, an authentic American dive bar complete with a mural of local hero Barack Obama. By now you’ll have earned a serious meal, so catch the L back into the heart of town to Café Spiaggia, a classy joint with an unparalleled view over Lake Michigan, where you can enjoy a late lunch of steaming fresh clams in a rich garlic and parsley sauce.


5 p.m. - Your final stop should be the Signature Lounge across the street, where you can sip a well-earned farewell drink - perhaps a specialty Summer Blossom Martini - while enjoying its legendary view of the heart of the city.


If you have more time…

This guide is just the start of what Chicago has to offer, and there are plenty of other places to go and things to see. If you find yourself with a little extra time, check these places out:


Old Lviv – There’s a historic Ukrainian community in Chicago, and this fantastic little restaurant is right in the heart of the “Ukrainian Village” district.


DuSable Museum –One of the oldest museums of African American history in the country, conveniently situated in Hyde Park.


Oriental Institute Museum – A fabulous and extensive collection with free entry, well worth the trip on the L train.


Shedd Aquarium – Sharks, piranhas, turtles and more in a recently revamped space including a realistic river habitat.


Portillo’s – A Chicago institution known for its hot dogs.


The Field Museum – A large natural history museum right in the heart of town.


Navy Pier – Plenty of shops, restaurants and a cinema, as well as the Chicago Shakespeare Theater.


Adler Planetarium – Adjacent to the Navy Pier, famous for its “Sky Theater”, which shows mind-bending virtual reality shows.


Brookfield Zoo – A long way out of town but worth it. An enormous (217 acre) site which is home to almost 6,000 animals.


Location/contact details:

Day one

Wrigley Field

1060 West Addison Street, Chicago, IL 60613

(773) 404-2827



730 North Rush Street, Chicago, IL 60611

(312) 951-0747


Smart Bar

3730 North Clark Street, Chicago, IL 60613

(773) 549-4140


Music Box Theatre

3733 North Southport Avenue, Chicago, IL 60613

(773) 871-6607


Day two

Willis Tower

233 South Wacker Drive, Chicago, IL 60606

(312) 875-0066


Frontera Grill

445 North Clark Street, Chicago, IL 60654

(312) 661-1434


The Art Institute of Chicago

111 South Michigan Avenue, Chicago, IL 60603

(312) 443-3600


Chicago Cultural Center

78 East Washington Street, Chicago, IL 60602

(312) 744-6630


Max's Take Out

20 East Adams Street, Chicago, IL 60603

(312) 553-0170


City Gallery in the Historic Water Tower

806 North Michigan Avenue, Chicago, IL 60611

(312) 742-0808


Day three

Museum of Science and Industry, Chicago

5700 South Lake Shore Drive, Chicago, IL 60637

(773) 684-1414


Cove Lounge

1750 East 55th Street, Chicago, IL 60615

(773) 684-1013


Cafe Spiaggia

Level 2, 980 North Michigan Avenue, Chicago, IL 60611

(312) 280-2750


The Signature Lounge at the 96th

875 North Michigan Avenue, Chicago, IL 60611

(312) 787-9596


Other tips

Old Lviv

2228 West Chicago Avenue, Chicago, IL 60622

(773) 772-7250


DuSable Museum of African American History

740 East 56th Place, Chicago, IL 60637

(773) 947-0600


Oriental Institute Museum

1155 East 58th Street, Chicago, IL 60637

(773) 702-9520


Shedd Aquarium

1200 South Lake Shore Drive, Chicago, IL 60605

(312) 939-2438



100 West Ontario Street, Chicago, IL 60654

(312) 587-8910


The Field Museum

1400 South Lake Shore Drive, Chicago, IL 60605

(312) 922-9410


Navy Pier

600 East Grand Avenue, Chicago, IL 60611

(312) 595-5282


Adler Planetarium

1300 S Lake Shore Dr, Chicago, IL 60605

(312) 922-7827


Brookfield Zoo

8400 West 31st Street, Brookfield, IL 60513

(708) 688-8000