It’s likely hard to find a midwest travel list that doesn’t include Chicago travel. As one of the most populated cities in the region, there’s plenty to see and do in the Windy City. Not only can you find fun sites and attractions to explore, but the city hosts one of the best culinary scenes in the US.

As you might expect with a major city, pro sports are in full force year-round. Whether it’s the Bulls, Blackhawks, Bears, White Sox, Cubs, or Fire FC, you can get your fix any time of year. Before diving into this Chicago travel guide, let’s cover which credit cards to bring with you on your Chicago trip.

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Best Credit Cards to Use in Chicago

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Amex, Chase, and Citi have dominated the travel credit card landscape. Now, add Capital One’s to the mix with the addition of new transfer partners and transfer ratios for some partners changing to 1:1. Some of the more interesting cards from these banks include the Amex Gold Card, Chase Sapphire Reserve, Citi Premier Card, and Capital One Venture.

You earn 4x points at restaurants and US grocery stores with the Amex Gold card. The Chase Sapphire Reserve earns 3x points at restaurants and on travel. Citi Premier cardmembers 3x points on restaurants, supermarkets, gas stations, air travel and hotels. You earn 2x miles (points) on every purchase with the Capital One Venture.

What is the best month for Chicago travel?

May through October are some of the best times for Chicago travel. Temperature ranges in the 60’s for the high and low 50’s for the low in the shoulder months of May and October. June to September range from the upper 70’s to low 80’s for the high and low 60’s to low 70’s for the low.

Unless you thoroughly enjoy cold weather, you can skip November to April. Having visited multiple times in this timeframe, I can attest that it can get bone-chilling cold. Cold football games can be a novelty but other than that, stick to May to October for your Chicago travel.

How to Fly to Chicago

There are two major airports in O’Hare International Airport (ORD) and Midway International Airport (MDW) when traveling into Chicago. O’Hare is generally considered the international airport while Midway is generally a US-centric airport. Most major US airlines fly into these airports so here’s a rundown of the non-stop flights you can book.

• O’Hare International Airport
  • Alaska Airlines <> Boise, Los Angeles, Portland (OR), San Francisco, Seattle/Tacoma
  • American Airlines <> Cities include Austin, Denver, London–Heathrow, Los Angeles, Miami, Nashville, New Orleans, New York–JFK, New York–LaGuardia, Portland (OR), San Diego, San Francisco, Seattle/Tacoma
  • Delta Air Lines <> Cities include Atlanta, Detroit, Minneapolis/St. Paul, New York–JFK, New York–LaGuardia, Salt Lake City, Seattle/Tacoma
  • JetBlue <> Boston, Fort Lauderdale, New York–JFK, West Palm Beach
  • Southwest Airlines <> Baltimore, Dallas–Love, Denver, Fort Myers, Las Vegas, Nashville, Orlando, Phoenix–Sky Harbor, Tampa
  • United Airlines <> Cities include London–Heathrow, Los Angeles, New York–LaGuardia, Paris–Charles de Gaulle, San Francisco, São Paulo–Guarulhos, Tel Aviv, Tokyo–Haneda, Washington–Dulles, Zurich
• Midway International Airport
  • Delta Air Lines <> Atlanta, Detroit, Minneapolis/St. Paul
  • Southwest Airlines <> Cities include Austin, Destin/Fort Walton Beach, Los Angeles, Miami, Montego Bay, Portland (ME), Portland (OR), San Francisco, San José del Cabo, San Juan, Washington–National

Where to Stay When Visiting Chicago?

All four major points hotel brands in Hilton, Hyatt, IHG, and Marriott offer a variety of options for your Chicago travel. We like to stay around the River North neighborhood as it offers easy access to the sites and restaurants around the city.

Hotels that look interesting include Hilton’s Palmer House and LondonHouse. Hyatt has the Chicago Athletic Association and the Park Hyatt. Use your IHG points to book the Kimpton Hotel Monaco or Kimpton Gray Hotel. Marriott properties that have flare include The Blackstone and The Gwen.

Chicago Places to Visit in 48 Hours

Day 1

Your Chicago travel kicks off with caffeine from one of Chicago’s 20 Essential Coffee Shops. With coffee in hand, walk Millennium Park and snap a pic in front of Cloud Gate (the bean). Continue down to Grant Park before lunch from a restaurant in the 38 Standout Dining Destinations in Chicago.

In the afternoon, make your way to the top of the Willis Tower to see for miles in every direction from the Skydeck. Grab a drink and walk the Chicago Riverwalk after exploring the Skydeck. Head back to the hotel to regroup or hop right on board a Wendella Tours & Cruises boat. The sunset views are unbeatable. Pick a spot from 38 Standout Dining Destinations in Chicago or Michelin Guide Chicago to close out day 1.

Day 2

Caffeinate yourself at one of Chicago’s 20 Essential Coffee Shops to start your second day. Navy Pier is up first followed by the Ohio Street Beach. Relax on the beach and snap pictures of the incredible Lake Michigan. When your R&R is complete, fuel up at one of the 38 Standout Dining Destinations in Chicago.

If the season is right, catch an afternoon Cubs game at Wrigley Field, a Bulls or Blackhawks game at United arena, or Bears game at Soldier Field. Your 48 hours of Chicago travel ends with dinner at one of the 38 Standout Dining Destinations in Chicago or Michelin Guide Chicago restaurant.

Chicago Travel FAQs

Are there weekend trips from Chicago?

Check out Best Weekend Getaways From Chicago and 10 Best Weekend Getaways From Chicago for inspiration.

What day trips from Chicago can you take?

See 5 Best Day Trips from Chicago and Top 7 day trips from Chicago to determine what makes sense for you.

What are the best road trips from Chicago?

Read through 6 Best Road Trips From Chicago to get your fix.

Conclusion on Chicago Travel

A Chicago trip in 48 hours is clearly not enough time. So add in a third, or hey, even a fourth day if you need it! Holding the right credit cards is king, especially ones with high earn rates when you’re eating at Chicago restaurants. Generally speaking, the summertime is the best season for Chicago travel. Two major airports serve the city and there are plenty of points hotels you can book.

What do you think of this Chicago travel guide? What other US cities do you recommend visiting? Please let me know in the comments below or by sending me an email on my contact page.

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