to BOS at To view the purposes they believe they have legitimate interest for, or to object to this data processing use the vendor list link below. travelers, you can enter the sum of everyone's value. If you go between April and May in the spring, you'll catch the beginnings of festival season, along with milder weather and a far lower number of fellow tourists. Also keep in mind that traffic will delay you, and if you leave Boston during rush hour or on a Friday or Saturday, you'll have a harder time getting out of the city. By joining our email list, you give LazyTrips permission to use your email for sending you newsletters, emails and updates including for marketing purposes. you stay overnight, the important thing is the total sum of If you're planning a road trip to Chicago, you can research locations to stop along the way. Fun things to do South Bend (7 answers). Since this is a long drive, you might want to stop halfway and stay overnight in a hotel. You could also include an extra cost for food at the airport, Bing Maps, or The consent submitted will only be used for data processing originating from this website. To change the price for your flight, enter it here: Enter the total amount you're planning to spend Famous place to eat at? View a map with driving directions Syracuse (New York) (14 answers) Of course, you'll need to be prepared to encounter heavy traffic moving in and out of NYC. There are definitely some places you should make a point of trying to stop at, though. who wants the trip to end? by calculating the distance from Chicago to Boston. you can get answers personalized for your tastes, budgets, Road trip starts at Chicago, US and ends at Boston, US. Travelmath helps you find the driving value of your time spent traveling. Our score includes factors The city of Pittsburgh was built on pretty hilly terrain, and as a result boasts the second highest number of stairs in any city. You might also want to catch a show at the Landmark Theater or check out the Erie Canal Museum. stay for about 1.5 hours and leave at 2:07 pmdrive for about 2 hours, 4:12 pm Erie Fun things to do Driving is usually cheaper, but it takes a lot longer. Is There a Bus That Goes From Boston to Chicago? Thinking of taking this epic road trip? Seeing the Midwest without having to drive, Extended road trips; exploring the local area. Book a room at the Renaissance Toledo Downtown Hotel, where it's just a 10-minute drive to the Toledo Zoo. Try deep dish pizza and Chicago-style hot dogs. Niagara Falls (65 answers) Is the Boston Freedom Trail worth a visit? Syracuse (New York) (14 answers) Consider booking a room at the Ritz-Carlton, where you'll enjoy an on-site fitness center and restaurant at this classy hotel. Depending on the route, flying can be the most cost-friendly option as well. Your road map begins at Chicago, US and ends at Boston, US. Enter the total amount you're planning to used to calculate the sum of plane tickets for everyone, as well This road trip will have you spending 983 miles and 15 hours of pure driving. It ends in Boston, Massachusetts. on extra costs for local transportation at your destination. We estimated the cheapest price for a round trip plane to estimate the wear and tear on your car. Where's a fun place for breakfast in Toledo Ohio? and hotels is the Trippy page on Here are some more restaurants people talk about: Want to research more popular restaurants in Chicago? how far is it to drive from Chicago to Boston with full directions. various rules for standard mileage rates. because there's an entire community of travelers talking Here are some more hotels people talk about: Want to research more popular hotels in Boston? Enter a city to drive through, or find all. The Greenhouse Tavern These are some of the places people talk about on Trippy: Of course, Trippy is the perfect place to ask questions Book a room at the Renaissance Toledo Downtown Hotel, where it's just a 10-minute drive to the Toledo Zoo. Otherwise, continue eastwards by staying on the I-90 past Syracuse, Albany and Springfield. The cheapest way to get from Chicago to Boston is to drive which costs $95 - $140 and takes 9h 1m. Multiple airlines fly from Boston to Chicago (Chicago OHare International Airport or Chicago Midway Airport) every hour. I-90 and I-80 (which run together in Ind and OH) split near Cleveland, with I-90 heading northeast, up through Erie PA, Buffalo NY, and continuing through upstate NY and then the Berkshires in Mass. But what's the point of taking a road trip if you're not going to stop and appreciate the places you're passing? hotels around Cleveland: Your trip begins in Chicago, Illinois. Explore! a max of 4 passengers per car, but you West Side Market (6 mentions) This is a great opportunity to take a longer break from driving. Boston is located in United States with (42.3584,-71.0598) coordinates and Chicago is located in United States with (41.85,-87.6501) coordinates. trip dates & more! the results with the flight time calculator to see how much This is equivalent to 1 369 kilometers or 739 nautical miles. The Windy City has much to see, do, and eat. Remember to leave enough time to get through security lines. And as an added bonus, you'll be right next to I-190 ready for your onward trip to Niagara Falls the next morning. (59 answers), Sunil from Mountain View asked:Best Chicago pizza? The quickest way to get to the Windy City is to fly, which will take you about 4 hours, 42 minutes. Leave Boston via the I-90, following this highway across Massachusetts until you reach the Hudson River in New York State. the Buffalo Marriott at LECOM HARBORCENTER is a stand-out choice thanks to its perfect location. If you decide on routing your trip via Niagara Falls, then Buffalo is a logical stopover point - just 30 minutes away. You can also check the cost of driving from Chicago to Boston. Your email will not be provided to third parties. Find out how many days in Chicago to stay. from Chicago to Boston. The total driving distance from Chicago, IL to Boston, MA is 982 miles or 1 580 kilometers. You'll also get the chance to check out some of Boston's fall events, like the Boston Film Festival or the Phantom Gourmet Food Festival which both take place during September. depending on your preference. Continue with Recommended Cookies. restaurants around Cleveland: September and October are also good months to visit. However, when deciding whether or not this is the optimal route for you, you should consider the costs of gas, tolls, and a hotel. But you'd have to skip every sight you're passing, and you'd be on a very tight schedule. 50 cents per mile for business travel, and the IRS has Distance between Chicago and Boston is 1368 kilometers (850 miles).Driving distance from Chicago to Boston is 1580 kilometers (982 miles). If you want to experience the festive atmosphere of Chicago while having to cope with fewer crowds, going during one of the shoulder seasons might be best. questions about Niagara Falls: Set this to zero if you're renting a car. $318. The best resource on neighborhoods, areas, Traveling with a dog or cat? Best way to get to downtown Boston from Logan Airport. This hotel has a bar, restaurant, indoor pool and fitness center, and is close to many of Syracuse's attractions. (9 answers). Make sure to take some time to visit the Cleveland Museum of Art, as well as the West Side Market when you start getting hungry. Note: Clicking on any of the directions above, will automatically zoom in on that location within the map. Amtrak services this direct route. What is your favorite restaurant in Chicago. What should I wear? What is one attraction to see? (18 answers), Blair from Halifax asked:What to do in one weekend in Chicago? While Hotel Zachary offers views of famed Wrigley Field, Swissotel Chicago overlooks the Chicago River. Cleveland is the first major city that both of our route options pass through, around 5 and a half hours into the journey. We estimate you'll need to stay at a hotel This might be the best option for those who don't want to drive or fly. From: 1 traveler 2 travelers 3 travelers 4 travelers 5 travelers 6 travelers. While in Buffalo, we'd recommend you soak up the city's first-rate architectural and botanical attractions: namely Frank Lloyd Wright's Martin House and Buffalo and Erie County Botanical Gardens. You will finally reach Boston around 7 hours after leaving Buffalo. After around 5 hours and 15 minutes you will reach Cleveland, a great stop for a late lunch or and afternoon spent stretching your legs. Coffee. would cost you to take a flight, including factors to account We assume a max of 4 passengers per car, but Compare Some airlines require you to check-in Your trip begins in Chicago, Illinois. Take the I-90 eastwards out of Chicago, passing South Bend, Elkhart and Perrysburg. New to the city, friend coming to visit: What should we do? leave the next day around 11:00 am, 11:00 am leave from The Cleveland Hostel Enter the fuel efficiency of your vehicle in Continue through Cleveland, following the I-90 the rest of the way across Ohio and northern Indiana before finally reaching Chicago. Great Lakes Brewing Company (5 mentions) and hotels is the Trippy page on The calculated flying distance from Chicago to Boston is equal to 850 miles which is equal to 1368 km. destination after you've landed at the arrival airport. Fun Fact: In 1765, John Harrison and James Baker made the first chocolate products in America in a sawmill in the Lower Mills district of Boston. You can also compare the travel time if you're flying or driving (10 answers), Sara from Westerly asked:Where are the best shopping deals in Boston? because there's an entire community of travelers talking From here, take the CT-15 to Hartford before merging onto the I-94 and then I-90. stay for about 1 hour and leave at 4:19 pmdrive for about 1.5 hours, 5:59 pm arrive in Chicagoeat at Lou Malnati's Pizzeria If you're planning on spending the night in Syracuse, check out Aloft Syracuse Inner Harbor. You can also include the cost of ticket from ORD Can we take food across the US/Canada border on our road trip to Niagara Falls? stay for about 1 hour and leave at 1:39 pmdrive for about 2 hours, 3:51 pm Albany (New York) This might include a rental car to drive around the area, or Melt Bar & Grilled What is your favorite restaurant in Cleveland? If you're planning a road trip to Chicago, you can research locations to stop along the way. You'll be spending a lot of time on the road, going across several states before reaching your destination. Maid of the Mist (5 mentions) Lola Train tickets may be purchased online or in-person at the train station. miles per gallon (mpg). you plan the best route to travel to your destination. Pittsburgh itself is easily worth an overnight stop - or at least a few hours - with its fabulous foodie scene which perhaps belies its status as the home of the Big Mac. Customers . New to the city, friend coming to visit: What should we do? You'll get the tail end of the city's warm summer weather, with temperatures averaging between the 60s and 70s Fahrenheit. Gas. trip dates & more! speed travel time table on the right for various options. Erie (2 answers) This section could be endless, so rather than trying to If you want to go by car, the driving distance between Boston and Chicago is 1578.8 km. While you're in the city, check out the Toledo Museum of Art in the Old West End. Camping along the way? (9 answers), Hannah from Milwaukee asked:What are the can't miss things to do in Boston? You might be more interested in calculating the The total driving time is 14 hours, 47 minutes. Find pet-friendly stops. questions about Albany (New York): and an estimate of your car's best gas mileage. Worried about Boston cold weather. or Sydney, and get inspired for your dream trip around the world. and answers related to Boston. Rock and Roll Hall of Fame and Museum (13 mentions) Located on the shore of Lake Erie, Toledo boasts a zoo, museums, and parks to explore. stay for about 1 hour and leave at 4:51 pmdrive for about 3 hours, 7:46 pm arrive in Bostoneat at Mike's Pastry There is a Greyhound that goes from Boston to Chicago, though you will have to transfer in New York City. Click the blue button below. Driving non-stop from Boston to Chicago How far is Chicago from Boston? Or get a full Chicago to Boston flight plan. The entire journey from Boston's busiest hub, South Station, to Chicago Union Station takes 22 hours. Still want more flight details? If you opt for this, be sure to talk to the rental agency and have it put into your contract. Plus, if youre traveling with a companion or kids, you can socialize instead of focusing on the rules of the road. Merge onto I-95 and travel north through Connecticut until you reach Bridgeport. Need some recommendations on somewhere to get food? drive for about 2 hours, 11:46 am Toledo (Ohio) stay for about 1 hour and leave at 4:10 pmdrive for about 2 hours, 5:59 pm Cleveland Where's a fun place for breakfast in Toledo Ohio? If you are looking for a chance to sample some urban charm, culinary genius and a dose of history, then we'd recommend you take the Pittsburgh Route. Avoid traffic with optimized routes. You'll only be 0.6 miles from Destiny USA, and 0.8 miles from Clinton Square. Search for RV campgrounds. Best and most affordable hotel with bar and hot tub? Lolita Make sure you include extra time to get to the rental Enter the total number of travelers. by calculating the distance from Boston to Chicago. Here are a few of our favorite options for places to stay on your journey. But now it turns out we can leave Friday afternoon around 3 pm, with the goal of getting to Boston at some point before 6 pm on Monday. You'll get a view of downtown in this beautiful hotel, and if you're planning on taking your dog on this trip, not to worrythis hotel is pet friendly. Road trip planner. On the other hand, going in the summer will mean a lot of crowds. Drive from Boston to Chicago 16h 30m $180 - $270 Quickest way to get there Cheapest option Distance between Boston to Chicago by train The train journey time between Boston and Chicago is around 22h 22m and covers a distance of around 1021 miles. Or maybe you'd like to see a more detailed driving directions map? If you're looking for a quick answer, you can check out The James Chicago Hotel, which was mentioned 12 times on Trippy. Lolita Driving 996 miles is quite the road trip. From November to March, you'll have to deal with snow and low temperatures as you drive. Live hits the road on June 25th in Boston, MA at TD Garden before stopping in Brooklyn, NY at Barclays Center on June 27th, rolling through arenas across the U.S. and Canada, and closing out on September 3rd in Los Angeles, CA at Kia Forum. We chose Chicago O'Hare International Airport (ORD) as your departure airport. If you're unsure of the exact number, For a flight, the straight line geographic midpoint coordinates are 42 25' 4" N and 79 . You can toggle between map views using the buttons above. Difference between fly and go by a car is 212 km. There are multiple ways to travel from Boston to Chicago, a distance of 996 miles. Niagara Falls (18 mentions) flight time from Chicago, IL to Boston, MA. Your email will not be provided to third parties. Get Driving Directions, Live Traffic & Road Conditions - MapQuest Food Shopping Coffee Grocery Gas Advertisement Directions Get step-by-step walking or driving directions to your destination. premium or diesel fuel prices. like airline prices and fuel costs, but it also takes into account the per mile. The total cost of driving from Chicago, IL to Boston, MA (one-way) is $157.81 at current gas prices. Head over to West Side Market which features more than 100 different vendors. Trip (983.9 mi) on Map Chicago Boston. New York City is the most popular city on the route it's 12 hours from Chicago and 4 hours from Boston. If you're planning a road trip to Boston, you can research locations to stop along the way. The exact coordinates of the midpoint are: 42 28' 24" N 79 16' 38" W. The best place to meet based on recommendations from Trippy members is Jamestown (New York). Get the reverse directions for a This is based on typical traffic conditions for this route. or stopping at restaurants, and any other miscellaneous because you have to drive an extra day, it might be better to fly Make sure to also spend some time in the Toledo Botanical Garden, which consists of 50 acres of beautiful blooms. What's the best neighborhood in Cleveland for a first time visitor? Get our travel tips Delivered to your inbox. So we include the Even when you factor in the time it takes to get to Boston Logan International Airport, check in, and go through security, flying is still the most efficient option. The default is . one below. Situated in the heart of downtown Buffalo, the hotel places you right where you need to be for an evening spent making the most of the city and its stunning Lake Erie waterfront. value of your time spent in the car, as well as additional costs The Greenhouse Tavern By Teodor Hllestrand in forum Planning Summer RoadTrips, By t1m in forum Planning Summer RoadTrips, By stardust in forum Fall & Winter RoadTrips, By docsmith in forum Fall & Winter RoadTrips, By iierjii in forum Fall & Winter RoadTrips, Driving from Chicago to Boston over 3 days, Delaware Water Gap National Recreation Area, Questions & Comments about using this Forum, 2 Swedes driving LA -> SF -> LV -> Chicago -> Myrtle Beach, South C in 21 days, First roadtrip: we need YOUR help! stay at The James Chicago Hotel, Albany (New York) (14 answers) drive for about 2.5 hours, 12:39 pm Syracuse (New York) Driving Directions from Chicago to Boston Road trip starts at Chicago, US and ends at Boston, US. Cleveland (69 answers) Food. You can find the city that is halfway between Chicago, IL and Boston, MA. What is your favorite restaurant in Cleveland? While flying may be quicker, it's always more cost efficient to drive to your destination so you may want to calculate the fuel cost from Chicago to Boston. stay for about 1 hour and leave at 5:12 pmdrive for about 2 hours, 7:00 pm Cleveland The total route from O'Hare to Forest Park terminal in downtown Chicago takes 40 minutes. eat at Lola Good news! Depending on the time you have available, you might choose to stop over in Philly or continue on northwards - via the I-95 - to New York City. you longer to get there if you're driving. Cleveland (69 answers) Explore the city's famous bridges, historic industrial architecture and take on its record-breaking number of stairs. Additionally areas of Boston might be highly elevated which can make it more difficult to drive there How elevated? out how long it will take to drive between any two cities, Niagara Falls (65 answers) hand, you may want to focus more on typical maintenance Ice and snow can make the roads unsafe, and many of the parks you might want to check out will be closed. questions about Albany (New York): As you travel on I-90 west, youll touch five states before reaching Illinois: Massachusetts, New York, Pennsylvania, Ohio, and Indiana. This gives passengers many options when it comes to price and departure times. The 980-mile road trip from Boston to Chicago will take at least 15 hours of driving across Massachusetts, upstate New York, Ohio and Indiana. Enter the total number of cars you'll be Are you going straight to a hotel, or try changing your destination. When you arrive in NYC, transfer to a Greyhound bound towards the Chicago Amtrak, II station. stay for about 1 hour and leave at 12:38 pmdrive for about 2.5 hours, 3:10 pm Toledo (Ohio) What's the best neighborhood in Cleveland for a first time visitor? Snowfall can make your drive more difficult, or impede it altogether. Take a few days to explore National Parks and towns on Lakes Erie and Michigan or detour via Niagara Falls. Don't forget about exploring your own hometown with a staycation. So take a look at the travel time from Chicago to Boston. Tap on a 4:13 pm arrive in Boston (Indiana) day 2 driving 3 hours. Great Lakes Brewing Company (5 mentions) The 980-mile road trip from Boston to Chicago will take at least 15 hours of driving across Massachusetts, upstate New York, Ohio and Indiana. 14 hours, 47 minutes Find out how many hours from Chicago to Boston by car if you're planning a road trip. What is your favorite restaurant in Cleveland? The calculated flying distance from Boston to Chicago is equal to 850 miles which is equal to 1368 km.. In the summer, you'll have warmer weather and a much more pleasant drive, but this will also bring more tourists to Boston. You can adjust any of the settings above to customize the taking on the road trip. Rock and Roll Hall of Fame and Museum (13 mentions) Report inappropriate content 1-4 of 4 replies Sorted by 1 bobnIL Chicago, Illinois Level Contributor 4,053 posts 38 reviews 9 helpful votes 1. Enter the amount of time it takes you to get to your Consider booking a room at the Ritz-Carlton. Directions to Boston, MA . Show only these on map 1 Detroit Save On2lists If you want to go by car, the driving distance between Chicago and Boston is 1580.05 km. driving distance = 982 miles Driving directions from Chicago to Boston From: To: What's the distance? Explore art museums like the Art Institute of Chicago and the Museum of Contemporary Art Chicago, or take the whole family to the Lincoln Park Zoo, Shedd Aquarium, and Field Museum. open-ended. Leaving Albany, NY for 6 days, north or south? If you're planning on spending the night in Syracuse, check out Aloft Syracuse Inner Harbor. This is somewhat expensive compared to other train fares, but it makes sense given the route's long distance. So in this case, it's better to The Chicago Architecture Foundation River Cruise is fantastic as well and offers insight into the citys incredible architecture. green Buses on this route leave hourly. travelers and answer their questions about Chicago! Check out live theatre and comedy like Broadway in Chicago, Royal George Theatre, Drury Lane Theatre, Marriott Theatre, and The Second City. Niagara Falls (18 mentions) The quickest way to get to the Windy City is to fly, which will take you about 4 hours, 42 minutes. Wendy Altschuler is a Chicago-based travel and lifestyle writer who covers adventures across the globe. This way, you can drive more leisurely, and take your time checking out the parks and cities you're going to be driving past. Click on any question to see answers from the community! To get to NYC, first head to Bostons South Station bus terminal (a 2 minute walk from the train terminal). It's okay, you can start planning your You can also compare the travel time if you're flying or driving We'd recommend taking the I-278 and then I-478 to reach Manhattan and then crossing over to FDR Drive, skimming the east side of the island. Driving Directions to Boston, MA including road conditions, live traffic updates, and reviews of local businesses along the way. The total driving distance from Chicago, IL to Boston, MA is 985 miles or 1 585 kilometers. The bus leaves once a day and the journey will take approximately 20 hours. This is true for any of the other cities you're planning on stopping in. Chicago to Boston drive road conditions from Chicago to Boston flattest route from Chicago to Boston Plan your road trip at Change your driving speed: When it comes to choosing a route from Chicago to Boston, your 'best' option will depend on the vacation vibe you are seeking. Kilometers per hour: 106.8 km/h Traveling with a dog or cat? open-ended. leave the next day around 10:00 am, 10:00 am leave from The Cleveland Hostel Best and most affordable hotel with bar and hot tub? You might Traffic might also slow you down, so make sure you're allotting yourself enough time to deal with any traffic delays you might encounter. Click the button below to explore more questions Toledo Zoo (2 mentions) depending on whether you take a cab, get a ride from a friend, or drive by a certain time if you haven't done it online beforehand. The Cleveland Hostel By joining our email list, you give LazyTrips permission to use your email for sending you newsletters, emails and updates including for marketing purposes. you can change the number of cars if your situation is different. for every 12 hours of driving, and the average cost of a hotel The default or Sydney, and get inspired for your dream trip around the world. to include. We chose Boston Logan International Airport (BOS) as your arrival airport. costs and depreciation, which might be closer to 10 cents If you're taking a long road trip, the The distance between Chicago (Chicago Midway International Airport) and Boston (Logan International Airport) is 861 miles / 1385 kilometers / 748 nautical miles. next trip! Instead, consider visiting this city in the fall. spending along the way. The Cleveland Museum of Art (12 mentions) stay overnight and leave the next day around 10:00 am, 10:00 am leave from Syracuse (New York) Enter the amount of time you plan to allow for L'Albatros Because the route is so long and it's hard to predict delays, it's best to split it into 3 or 4 days. We have planned to take 4 to 5 nights for this part of our trip. North of Buffalo, you have the option of diverting slightly (and we'd strongly recommend this) to Niagara Falls by taking the I-190 for just 30 minutes out of the city. Here's the quick answer if you have friends taking shifts as driver so that you can make the entire trip by car without stopping. You'll be glad you skipped out on the stress of trying to complete a 15-hour road trip in a day and allowed yourself to enjoy the journey. stay overnight and leave the next day around 10:00 am, 10:00 am leave from Niagara Falls Please check the avg. The driving distance from Chicago (MDW) to Boston (BOS) is 994 miles / 1600 kilometers, and travel time by car is about 18 hours 46 minutes. The best route will take you along the shores of Lake Erie, allowing you to stop at Niagara Falls before continuing along past Cleveland towards Chicago. check-in at the airport. Make sure you check road conditions where to stay in Boston. Distance between Boston and Chicago is 1368 kilometers (850 miles).Driving distance from Boston to Chicago is 1579 kilometers (981 miles). * Due to road conditions, road work and other unpredictable conditions, these directions should be taken as estimates. and any other miscellaneous spending along the way. You might also want to time your Boston visit to coincide with Oktoberfest if you go between September and October, which isn't something you'll forget anytime soon. you can look it up on the one below. Want to plan the trip back? Traveling with a dog or cat? The road map above shows you the route to take to your destination. It ends in Boston, Massachusetts. suggest every local activity or attraction, we'll leave it The fly or drive score is an estimate of the true cost of travel. Difference between fly and go by a car is 211 km. Take a few days to explore National Parks and towns on Lakes Erie and Michigan or detour via Niagara Falls. Enter your total estimate below. Take a tour of Point State Park and, from there, hit the popular riverside trails. drive for about 2.5 hours, 12:37 pm Niagara Falls There are no buses that run directly to Chicago from Boston; if you choose to take a bus, you will have to transfer in New York, the total journey lasting roughly 20 hours. Best and most affordable hotel with bar and hot tub? You can get from Chicago O'Hare to downtown via the Chicago Transit Authority (CTA) Blue Line. longer it might take to drive the distance instead of flying. cost of tolls, food or snacks if you're bringing groceries Some companies might pay This can vary depending on whether you take a Katie from Los Angeles asked:What is your favorite restaurant in Chicago? When it comes to accommodation, the Buffalo Marriott at LECOM HARBORCENTER is a stand-out choice thanks to its perfect location. to double check the weather. From award-winning museums to kid-friendly favorites, this metropolis has something for everyone. Regular fuel costs are around $4.02 per gallon for your trip. The 980-mile drive from Chicago to Boston takes between 15 and 18 hours to drive. Trains are also comfortable, clean, and smooth. The Cleveland Hostel Manage Settings Some of our partners may process your data as a part of their legitimate business interest without asking for consent. Maybe try typing in a faraway location like London, Hong Kong, If you're having issues using the site, please enable JavaScript and refresh your browser. There are multiple ways to travel from Boston to Chicago, a distance of 996 miles. The round trip cost would be $315.61 to go from Chicago, IL to Boston, MA and back to Chicago, IL again. The length of this trip might discourage a lot of people from doing it by car, but driving from Boston to Chicago will be a rewarding experience that you won't forget. looking for a vacation rental or Airbnb? Here are some more hotels people talk about: Want to research more popular hotels in Chicago? for pit stops, rest stops, gas, naps, or detours along the way. The city of Buffalo also lies just a little over halfway along your road trip route, meaning that this stop breaks up your journey well: another good reason to stop and recharge. If you are flying into Chicago Midway, the CTA Orange Line will take you downtown in about 20 to 25 minutes. Think about the This will be true for the other cities you pass through, so make sure you allow for any traffic delays in your schedule.