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Travel on Point(s) is an independent, advertising-supported website. This site is part of an affiliate sales network and receives compensation for sending traffic to partner sites like This compensation does not impact how or where products appear on this site. Travel on Point(s) has not reviewed all available credit card offers on this site. Reviews, analyses & recommendations are the author’s alone and have not been reviewed, endorsed, or approved by any partner entities.

Chicago Travel Guide

Our friend Jim Fatzinger, The Travel Organizer, is back to discuss the Windy City, Second City, Chi-Town etc. in this Chicago travel guide. Last time he joined us he put together a great destination guide on visiting Santa Fe. That one is worth checking out too if you haven't already. In this Chicago destination guide Jim will discuss getting around the city, what to see, eat and do plus some other tips along the way. We hope you enjoy!

Getting From The O'Hare Airport To Downtown

I admit it. I have an affinity for destinations where one can see a lot of interesting things using public transportation (see “Practical Travel Tips: Oahu, Hawaii” and “Practical Travel Tips: Portland, Oregon”). In Chicago, four lines of the city’s “elevated” (usually and officially abbreviated as the ‘L’) rail service make a complete circuit around the downtown area, home to many of the city’s best-known attractions. It is this circuit that gives the heart of this great city its nickname – “The Loop.”

The Chicago Transit Authority’s (CTA) Blue Line from O’Hare airport intersects The Loop at Clark/Lake. (We actually rode one stop farther, to Washington, as this was more convenient for walking to our hotel (see below). Full price for this 50-minute, 17-stop ride is $5.00. However, my wife and I both qualify for CTA’s Reduced Fare Program for seniors, cutting our one-way cost to just $1.25. I loaded $5.00 onto each of our cards, and we ended up with balances of $1.40 after doing everything in this trip report!

Chicago Travel Guide: Where To Stay

We chose to stay at the Hyatt Place, Chicago Downtown/The Loop because:

  1. It was convenient to an ‘L’ stop. Since the weather was nice, we chose to get off at the Blue line Washington stop and walk 4 blocks west (past the Picasso sculpture) on West Washington Street, turning left (south) on North Franklin Street to our destination.
  2. It offered attractive amenities for the price point: a heated indoor pool, 24-hour fitness center, full-service bar in the lobby area, and a better-than-average complimentary breakfast.
  3. I earned 30,000 American Airlines Loyalty Points by booking through Rocketmiles. That’s 15% of the LPs needed for Executive Platinum status. Sadly, AA “enhanced” (= reduced) the number of LPs one can earn by booking hotels (and decimated earning through Rocketmiles!) shortly after our stay.
Thompson Chicago
Editor's Notes:

Mark here, I wanted to chime in on some Chicago hotel options. It really is a points lovers paradise with a lot of great hotels at reasonable points price. You have a Waldorf Astoria, Intercontinental and Park Hyatt in town, all at below ToP category pricing. That is if you want to go fancy at least.

What I really love about Chicago though, is the possibility of using free night certificates in the city. Something you can't do in other major metros like New York etc. My absolute favorite US Hyatt category 4 hotel certificate use is the Thompson Chicago. It is a bit outside of the magnificent mile, but the area is great and loaded with restaurants. The breakfast for Globalists at the Thompson is phenomenal too. If you prefer to be closer to the mile there is the Hyatt Centric as an alternate choice. If you prefer IHG then you can sometimes sneak in a stay at the Intercontinental with a 40K cert during the offseason. Getting value is Chicago is pretty easy, as long as you don't need to pay for parking. That is where they get you!

Chicago Travel Guide Day 1: Lobster Roll, Walking Tour, Romantic Dinner & Public Art

We had an action packed first day in the Windy City and we hit the ground running. Here are all the great things we were able to accomplish our first day. Here are our Chicago travel guide day 1 highlights.


After checking in (luckily, our room was ready early), we retraced our steps along West Washington Street to La Salle Street, where we turned left (north) to Luke’s Lobster City Hall. Rolls (lobster, crab, and shrimp) are the stars here. You can order them filled with either 4 or 6 ounces of your favorite shellfish or do as we did and order Luke’s Trio. That gets you 2-ounce rolls of each for $26.50. Yes, it’s a little pricey but Luke’s stuffs the rolls to overflowing. If we had to do it over again, we would probably order 4-ounce lobster rolls for $23.

Chicago Travel Guide
Free Walking Tour

One of the best things to do as early as possible when visiting a new destination is to sign up for a free walking tour (if any are offered). Such tours aren’t completely “free,” of course. Guides depend on tips, which are generally well deserved, for all or part of their compensation. Chicago Greeter is part of the International Greeter Association which started in New York City in 1992. Today, there are Greeter programs at 139 destinations in 38 countries. France, alone, has 52 Greeter programs while the U.S. has programs in just 4 U.S. cities: New York City, Houston, Denver, and Chicago. Their tagline is, “Come as a guest; leave as a friend!”

All Greeter tours are: (1) completely free – no tipping is allowed; (2) intimate – the maximum group size is 6; and (3) tailored to the guest’s interests – one completes a detailed form indicating areas of interest, lodging location, and time(s) available and the program matches you with a volunteer Greeter matching your profile. We were beyond thrilled with our experience as the Greeter assigned to us (Marianne Goss) led us to art-glass and mosaic installations in and around The Loop. The photo at left was taken looking up at one of the two Tiffany glass domes in the Chicago Cultural Center.


From our hotel, it was a short (3.5 blocks north, 2 blocks east, and cross the La Salle Drive bridge over the Chicago River) walk to get to River Roast which, as its name implies, offers applewood-smoked roast chicken, whole roasted fish (currently halibut and branzino), and slow-roasted portions (8 oz., 16 oz., or 24 oz.) of beef in a red wine Bordelaise sauce. The Happy Hour here is from 4pm-6pm, Monday through Friday with live music on Thursdays from 5pm-7pm.

  • Tip #1: Ask to be seated outside on their patio which offers stunning views of downtown and river traffic (wave to the tour boats as they cruise by).
  • Tip #2: Use OpenTable to make your reservation.
Public Art

Who knew? The world’s largest (and free!) permanent digital art display is in the Second City. The display transforms the 2.5-acre façade of Chicago’s Merchandise Mart on the north side of the Chicago River into a canvas twice nightly from April through December.  Past “Art on the Mart” shows have featured the Joffrey Ballet, Andy Warhol, Claude Monet, Cirque du Soleil, and “Ten Essential Chicago Bucket List Experiences”.

  • Tip: Because sunset varies with the seasons, be sure to consult the “Art on the Mart” website for showtimes during your visit.

Windy City Destination Guide Day 2: Millennium Park, Chicago Dog, Art Institute of Chicago & Food Hall

We tried to outdo day one with our day 2 exploring. Which one do you think was better? Here is our Chicago travel guide day 2 experience.

Millennium Park

Millennium Park, which sits atop one of Chicago’s major commuter rail terminals, is actually one of the world’s largest rooftop gardens. Bounded by East Randolph Street on the north, Michigan Avenue on the west, East Monroe Street on the south, and U.S. 41 on the east, Millennium Park is home to six unique public spaces which, explored in the order below, make an enjoyable, 2½-hour self-guided walking tour.

Cloud Gate

Start at the Cloud Gate (aka “The Bean”) in the northwest corner of this 24-acre public space : Liquid mercury is said to have been the artist’s inspiration for this 110-ton sculpture made up of 168 stainless steel plates welded into what has become one of Chicago’s most iconic symbols. Its highly polished exterior, with no visible seams, is cleaned daily and deep cleaned twice annually, using 40 gallons of detergent. The official website of the City of Chicago offers free MP3 audio tours for Millennium Park attractions; you can download/listen to the track for Cloud Gate here.

Jay Pritzker Pavilion

Walking from Cloud Gate toward Lake Michigan, the next attraction you come to is the Jay Pritzker Pavilion, designed by Frank Gehry. With a capacity of 11,000, this outdoor amphitheater offers free summer concert and film series. You can learn about the architectural design and the impact of that design on the listening experience here.

BP Pedestrian Bridge

Exiting Pritzker Pavilion at its southeast corner, you’ll find the 925-foot-long BP Pedestrian Bridge (also designed by Frank Gehry) which snakes over Columbus Drive. The length of the bridge makes it wheelchair accessible. You can learn more about its design, construction and the view this beautiful footbridge affords here.

Maggie Daley Park

The BP Bridge terminates in Maggie Daley Park which includes a “ribbon” (a meandering circuit instead of a traditional, oval rink) used for ice skating in the winter and scooters and roller blades in the summer, a climbing wall, Extreme Air Bungee, tennis courts, miniature golf, a play garden for children, a Cancer Survivor’s Garden, and picnic areas.

Lurie Garden

When you’re done exploring Maggie Daley Park, retrace your steps over the BP Bridge and turn left into Lurie Garden. Chicago’s slogan, “Urbs in Horto” (meaning “City in a Garden”) is exemplified by this oasis a stone’s throw from the skyscrapers lining Michigan Avenue. Learn more about the garden’s “dark plate,” “light plate,” “seam,” and “shoulders” here.

Crown Fountain

Crown Fountain is just on the other side of the north-south shoulder hedge in Lurie Garden. Here, the faces of 1,000 Chicagoans are projected onto LED screens inside the 50-foot-tall glass towers at either end of the fountain. When the weather is warm enough, these faces spew streams of water onto delighted children who play in the fountain.

Chicago Travel Guide
Chicago Hot Dog

Chicago-style hot dogs (all beef frankfurters, topped with yellow mustard, chopped white onion, sweet pickle relish, tomato, a dill pickle spear, sport peppers and celery salt in a poppy seed bun) should be on the menu for any carnivore visiting The Windy City. Everyone seems to have their own idea about who serves up the best dog, so we put two stands that get high marks on our itinerary.

To get to Relish Chicago Hot Dogs (4.5 « on Google reviews, Yelp!, and TripAdvisor) from Millennium Park, exit Crown Fountain and turn left (south) on Michigan Avenue past the Art Institute of Chicago to the corner of South Michigan Avenue and East Jackson Drive. You can’t miss the dark green stand at the corner of an adjoining park.  Order a dog that has been “dragged through the garden” (= with all the toppings above), chips, and soda/soft drink for just $7.50 and enjoy it on one of the park benches.

Chicago Travel Guide
Art Institute of Chicago

We spent all afternoon at the Art Institute of Chicago, but easily could have spent an entire day here and still not seen everything! The best known works here include Georges Seurat’s “A Sunday on La Grande Jatte” (Gallery 240), Van Gogh’s “The Bedroom” (Gallery 241), Edward Hopper’s “Nighthawks” (Gallery 262), Picasso’s “The Old Guitarist” (Gallery 391), Georgia O’Keeffe’s “Cow’s Skull with Calico Roses” (Gallery 265) and Grant Woods’ iconic masterpiece “American Gothic” (Gallery 263). The extensive Impressionist collection includes paintings by Monet, Manet, Degas, Cezanne, and Renoir. Don’t miss the Hartwell Memorial Window (pictured here) with its 48 panels depicting “…the transitory beauty of nature.”

  • Tip: Free 45-minute tours of selected works from the Michigan Avenue (Main) building are offered daily at 1:00pm; meet at the foot of the grand staircase below the Hartwell Memorial Window). Free tours of selected works from the Modern Wing are offered daily at 3:00pm; meet at the seating in Griffin Court. Every tour is different as guides are free to select works in areas of their expertise and/or interest.
Food Hall

Food halls are “a thing” in Chicago. We chose to visit Revival Food Hall because of its proximity to our lodging. Perhaps because of its location in the downtown core among office buildings, this seems to be a better choice for lunch than dinner. That is because everything closes by 7:00pm and only about half of the vendors were open at 5:00pm.

  • Tip: Consider joining the longest line; “regulars” know which vendors serve the highest quality/value.

Day 3 In Chi-Town: Museum Campus, More Chicago Dogs & Deep Dish Pizza

Are your feet already aching from all of this moving around? I know ours were by day 3 but we continued our treck in this amazing American city. Here are our Chicago travel guide day 3 highlights.

Museum Campus

Dusting off our CTA Reduced Fare passes, we walked 5 blocks east on Washington to its intersection with State Street and boarded Bus #146 whose outbound service terminates service at the Adler Planetarium on what is called “Museum Campus.” In addition to the Adler Planetarium, Museum Campus is home to Shedd Aquarium, the Field Museum, and Soldier Field. Cost: $1.10 each (with our CTA Reduced Fare passes).

In “Our Solar System,” the first exhibit after entering Adler Planetarium, you can touch a moon rock and a meteorite fragment as well as make a crater. The “Mission Moon” exhibit on the lower level simulates the choices involved in bringing the crew of Apollo 13 safely back to earth. In the dome theater, you can “tour” some of the most spectacular sights in our solar system or immerse yourself in a cosmic concert celebrating the 50th anniversary of “The Dark Side of the Moon” by Pink Floyd.

We could have spent an entire day at the Field Museum, one of the best natural history museums in the world. Probably the most famous dinosaur skeleton in the world, the Tyrannosaurus Rex named “Sue” (after the paleontologist who discovered “her” in South Dakota in 1990) has her own massive exhibit here. The man-eating Tsavo lions, whose story was sensationalized in the 1996 film The Ghost and the Darkness, also have their own exhibit here.

  • Tip: Stop by the information desk in the middle of the open hall on the main level where a knowledgeable volunteer will be happy to map out a route, tailored to your interests and the amount of time you have to visit.
Chicago Dog #2

The walk from Adler Planetarium to the Field Museum passes by Shedd Aquarium and leads to Kim and Carlos’ Hot Dog Cart where we tried our second Chicago-style hot dog. A combo (dog, chips, and drink) costs runs about $10.00.

Chicago Style Pizza

As it turns out, there is really no consensus among Chicagoans about their favorite style of pizza: deep dish (with the cheese on the bottom and the sauce on the top) or Tavern-style (round, thin crust pies often cut into squares instead of slices). Whatever your preference, the deep-dish variety served at Lou Malnati’s (Lou is the son of Rudy Malnati, often credited with making the first deep dish pizza in 1943 while chef at Pizzeria Uno) is absolutely heavenly. What makes it so special is its flaky, buttery crust. I kept wishing there was a way to create more crust surface; it’s that good! We walked from the Field Museum to the South Loop location at 805 South State Street.

  • Tip: Prepare yourself for a wait of 30 minutes or more; Lou Malnati’s pies are not made until they are ordered.
Editor's Note:

I will add in that my favorite pizza place in Chicago is Pequod's. While I enjoy Chicago style deep dish it isn't my favorite and I find Pequod's to be an interesting spin on it. It is almost like a merging of Chicago and Detroit style. It is worth the trip!

Maximizing Points, Miles, Discounts & Credits In Chicago

With a nod to the name of this website/blog, here are ways we earned/redeemed points or miles, snagged a discount, or earned credits for future flights/stays/dines, etc. on this trip:

  • Got free admission to the Adler Planetarium (saving $19/person) and the Field Museum (saving $30/person) from having a Traveler membership through the Kern County Museum in Bakersfield, CA. If you enjoy visiting museums on your travels, this is the best deal since sliced bread! For just $125, you get a year’s worth of complimentary admission for 2 adults and up to 4 children (ages 17 and under) to more than 1,000 (!) art and historical museums, botanical gardens, children’s museums, zoos, etc. We saved $98.00 on this trip alone!
  • Make reservations, whenever possible, using OpenTable. River Roast offers 1,000-point tables (worth $5.00 – $10.00 off a future dine) up until 5:00pm.
  • Airline clubs/airport lounges: We had direct flights, so we dropped into the Admirals Clubs in Charlotte and Chicago (courtesy of  AA’s Business Extra program) as well as The Club CLT (courtesy of Priority Pass).
Chicago Travel Guide

Architecture Cruise

The last editor note I will throw in here is the architecture cruises in Chicago. That was probably my favorite thing from our most recent trip and a great way to take in the city and learn about the history of it. I recommend the Chicago Architecture Cruise (which was recommended to me by a local). It is well worth the money and hit up The Northman before or after for a beer too!

Chicago Travel Guide: ToP Thoughts

We hope you enjoyed Jim's Chicago travel guide and have quite a few things to check off your list on your next visit to the Windy City. Chicago is sometimes the forgotten city but it is one of the best in the union. Especially if you make the trek in the summer months when you can enjoy the beaches and beautiful Lake Michigan.

Share some of your favorite Chicago travel tips over in the ToP Facebook Group. A big thanks again to Jim for putting this great Chicago destination guide together for us.


We promise to keep things short, sweet, and packed with awesome insights!